2-methylfuran-3-thiol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 0.57 Grams (0.0050 moles) of 2-methyl-3-furanthiol and 1.32 grams (0.01 moles) of n-heptylmercaptan are dissolved in 12 ml of diethyl ether. 0.8 Grams (0.0075 moles) of sodium carbonate dissolved in 8 ml water is added to the reaction mass. Over a period of 20 minutes, a solution of 1.9 grams (0.0075 moles) of iodine dissolved in 6 ml diethyl ether is added to the reaction mass with stirring until the iodine color remains. The reaction mass is then stirred over a period of 35 minutes. is added to the reaction mass is added to the reaction mass

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 0.57 Grams (0.0050 moles) of 2-methyl-3-furanthiol and 1.16 grams (0.01 moles) of cyclohexylmercaptan are dissolved in 12 ml of diethyl ether. 0.8 Grams (0.0075 moles) of sodium carbonate dissolved in 8 ml water is added to the reaction mass. Over a period of 10 minutes, a solution of 1.9 grams (0.0075 moles) of iodine dissolved in 6 ml diethyl ether is added to the reaction mass with stirring until the iodine color remains. The reaction mass is then stirred over a period of 45 minutes. is added to the reaction mass is added to the reaction mass

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Bromo-5-nitro-thiophene-2-carboxylic acid methyl ester ((Example 114, step c) 532 mg, 2 mmol), 2-methyl-furan-3-thiol (600 mg, 5.26 mmol), and DMAP-polystyrene resin (2 g, 2.86 mmol) were stirred in THF (10 mL) for 12 h at rt. The resin was filtered and washed with several portions of DCM (100 mL total volume). The filtrate was concentrated in vacuo and the yellow residue (480 mg, 80%) was used without further purification. 1H-NMR (CDCl3): δ 7.46 (d, 1H, J=1.9 Hz), 7.05 (s, 1H), 6.43 (d, 1H, J=1.9 Hz), 3.90 (s, 3H), 2.38 (s, 3H). The resin was filtered washed with several portions of DCM (100 mL total volume) The filtrate was concentrated in vacuo the yellow residue (480 mg, 80%) was used without further purification

反応条件: temp:33.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 50 ml round bottom 1 neck flask equipped with nitrogen inlet tube, "Y" tube, reflux condenser, magnetic stirrer, and cold water bath is placed a solution containing 0.54 g of sodium methylate (0.01 moles) in 6 ml of anhydrous methanol. 1.14 g (0.01 moles) of 2-methyl-3-furan thiol in 6 ml of anhydrous methanol is then added to the sodium methylate solution. The reaction mass is stirred for a period of 10 minutes, with cooling, maintaining the temperature thereof between 24° and 30° C. 0.91 g (0.01 moles) of a mixture of 80% 1-chloro-2-butene and 20% 3-chloro-1-butene dissolved in 2 ml of anhydrous methanol is then added over a 4 minute period warming to 33° C. The reaction mass is allowed to cool to 23° C. and remains at that temperature, with stirring, for a period of 2.5 hours, at which time it is concentrated to 7 ml on a rotary evaporator using water aspirator vacuum. 20 ml water is then added and the reaction mass is neutralized to a pH of 5 - 6 using 4% hydrochloric acid. The reaction mass is extracted with three 10 ml portions of n-hexane. The hexane extracts are combined, washed with 2 ml saturated sodium chloride solution, dried with anhydrous sodium sulfate and concentrated using a rotary evaporator to yield 1.24 g of a yellow oil. Into a 50 ml round bottom 1 neck flask equipped with nitrogen inlet tube "Y" tube, reflux condenser, magnetic stirrer, and cold water bath with cooling maintaining the temperature between 24° and 30° C is then added over a 4 minute period to cool to 23° C. with stirring, for a period of 2.5 hours, at which time it is concentrated to 7 ml on a rotary evaporator 20 ml water is then added The reaction mass is extracted with three 10 ml portions of n-hexane washed with 2 ml saturated sodium chloride solution dried with anhydrous sodium sulfate concentrated a rotary evaporator

反応条件: temp:33.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 50 ml round bottom 1 neck flask equipped with nitrogen inlet tube, "Y" tube, reflux condenser, magnetic stirrer, and cold water bath is placed a solution containing 0.54 g of sodium methylate (0.01 moles) in 6 ml of anhydrous methanol. 1.14 g (0.01 moles) of 2-methyl-3-furan thiol in 6 ml of anhydrous methanol is then added to the sodium methylate solution. The reaction mass is stirred for a period of 10 minutes, with cooling, maintaining the temperature thereof between 24° and 30° C. 0.91 g (0.01 moles) of a mixture of 80% 1-chloro-2-butene and 20% 3-chloro-1-butene dissolved in 2 ml of anhydrous methanol is then added over a 4 minute period warming to 33° C. The reaction mass is allowed to cool to 23° C. and remains at that temperature, with stirring, for a period of 2.5 hours, at which time it is concentrated to 7 ml on a rotary evaporator using water aspirator vacuum. 20 ml water is then added and the reaction mass is neutralized to a pH of 5 - 6 using 4% hydrochloric acid. The reaction mass is extracted with three 10 ml portions of n-hexane. The hexane extracts are combined, washed with 2 ml saturated sodium chloride solution, dried with anhydrous sodium sulfate and concentrated using a rotary evaporator to yield 1.24 g of a yellow oil. Into a 50 ml round bottom 1 neck flask equipped with nitrogen inlet tube "Y" tube, reflux condenser, magnetic stirrer, and cold water bath with cooling maintaining the temperature between 24° and 30° C is then added over a 4 minute period to cool to 23° C. with stirring, for a period of 2.5 hours, at which time it is concentrated to 7 ml on a rotary evaporator 20 ml water is then added The reaction mass is extracted with three 10 ml portions of n-hexane washed with 2 ml saturated sodium chloride solution dried with anhydrous sodium sulfate concentrated a rotary evaporator

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 25 ml round bottom flask equipped with magnetic stirrer, thermometer, reflux condenser and heating mantle is placed a solution containing 0.27 g (0.005 moles) of sodium methoxide in 3 ml of absolute methanol. With stirring and while maintaining the temperature at 25° - 30° C., 0.57 g (0.005 moles) of 2-methyl-3-furan thiol in 3 ml absolute methanol is added. The reaction mass is stirred for a period of 10 minutes. 0.86 g of benzyl bromide dissolved in 2 ml absolute methanol is then added to the reaction mass with stirring at 25° C. The reaction mass is heated to reflux (50° - 60° C.) and maintained at this temperature with stirring for a period of 4 hours. The reaction mass is then allowed to cool down to room temperature and is admixed with 10 ml of water with stirring. The reaction mass is neutralized to a pH of 5 - 6 with one drop of 10% hydrochloric acid and 5 ml hexane is added with stirring. The mass is then transferred to a separatory funnel and the organic and aqueous phases are separated. The aqueous phase is diluted with 5 ml water and extracted with 7 ml of n-hexane. The hexane extracts are combined, washed with 5 ml saturated sodium chloride, dried over anhydrous sodium sulfate, and gravity filtered. The resulting solution is then concentrated to an amber oil using rotary evaporation under a water aspirator vacuum. NMR, IR and Mass Spectral analyses confirm that the major product isolated by GLC trapping has the structure: ##STR36## Into a 25 ml round bottom flask equipped with magnetic stirrer thermometer, reflux condenser heating mantle while maintaining the temperature at 25° - 30° C. The reaction mass is stirred for a period of 10 minutes is then added to the reaction mass with stirring at 25° C The reaction mass is heated to reflux (50° - 60° C.) maintained at this temperature with stirring for a period of 4 hours with stirring is added with stirring The mass is then transferred to a separatory funnel the organic and aqueous phases are separated The aqueous phase is diluted with 5 ml water extracted with 7 ml of n-hexane washed with 5 ml saturated sodium chloride dried over anhydrous sodium sulfate, and gravity filtered The resulting solution is then concentrated to an amber oil evaporation under a water isolated by GLC trapping

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 25 ml round bottom flask equipped with magnetic stirrer, thermometer, water bath, and reflux condenser is added a solution containing 0.27 g of sodium methoxide (0.005 moles) in 3 ml. absolute methanol. While maintaining the solution at 25° - 30° C., 0.57 g (0.005 moles) of 2-methyl-3-furan thiol in 2 ml of absolute methanol is added thereto. At 25° C., 0.483 g (0.005 moles) of chloromethyl methyl sulfide having the formula: Into a 25 ml round bottom flask equipped with magnetic stirrer thermometer, water bath, and reflux condenser is added a solution While maintaining the solution at 25° - 30° C. At 25° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 25 ml round bottom flask equpped with magnetic stirrer, thermometer, reflux condenser and heating mantle is placed a solution containing 0.27 g (0.005 moles) of sodium methoxide in 3 ml of absolute methanol. With stirring and while maintaining the temperature at 25° C-30° C, 0.57 g (0.005 moles) of 2-methyl-3-furan thiol in 3 ml absolute methanol is added. The reaction mass is stirred for a period of 10 minutes. 0.86 g of benzyl bromide dissolved in 2 ml absolute methanol is then added to the reaction mass with stirring at 25° C. The reaction mass is heated to reflux (50° C-60° C) and maintained at this temperature with stirring for a period of 4 hours. The reaction mass is then allowed to cool down to room temperature and is admixed with 10 ml of water with stirring. The reaction mass is neutralized to a pH of 5-6 with one drop of 10% hydrochloric acid and 5 ml hexane is added with stirring. The mass is then transferred to a separatory funnel and the organic and aqueous phases are separated. The aqueous phase is diluted with 5 ml water and extracted with 7 ml of n-hexne. The hexane extracts are combined, washed with 5 ml saturated sodium chloride, dried over anhydrous sodium sulfate, and gravity filtered. The resulting solution is then concentrated to an amber oil using rotary evaporation under a water aspirator vacuum. NMR, IR and Mass Spectral analyses confirm that the major product isolated by GLC trapping has the structure: ##STR32## Into a 25 ml round bottom flask equpped with magnetic stirrer thermometer, reflux condenser heating mantle while maintaining the temperature at 25° C-30° C The reaction mass is stirred for a period of 10 minutes is then added to the reaction mass with stirring at 25° C The reaction mass is heated to reflux (50° C-60° C) maintained at this temperature with stirring for a period of 4 hours with stirring is added with stirring The mass is then transferred to a separatory funnel the organic and aqueous phases are separated The aqueous phase is diluted with 5 ml water extracted with 7 ml of n-hexne washed with 5 ml saturated sodium chloride dried over anhydrous sodium sulfate, and gravity filtered The resulting solution is then concentrated to an amber oil evaporation under a water isolated by GLC trapping

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 25 ml round bottom flask equpped with magnetic stirrer, thermometer, reflux condenser and heating mantle is placed a solution containing 0.27 g (0.005 moles) of sodium methoxide in 3 ml of absolute methanol. With stirring and while maintaining the temperature at 25° C-30° C, 0.57 g (0.005 moles) of 2-methyl-3-furan thiol in 3 ml absolute methanol is added. The reaction mass is stirred for a period of 10 minutes. 0.86 g of benzyl bromide dissolved in 2 ml absolute methanol is then added to the reaction mass with stirring at 25° C. The reaction mass is heated to reflux (50° C-60° C) and maintained at this temperature with stirring for a period of 4 hours. The reaction mass is then allowed to cool down to room temperature and is admixed with 10 ml of water with stirring. The reaction mass is neutralized to a pH of 5-6 with one drop of 10% hydrochloric acid and 5 ml hexane is added with stirring. The mass is then transferred to a separatory funnel and the organic and aqueous phases are separated. The aqueous phase is diluted with 5 ml water and extracted with 7 ml of n-hexne. The hexane extracts are combined, washed with 5 ml saturated sodium chloride, dried over anhydrous sodium sulfate, and gravity filtered. The resulting solution is then concentrated to an amber oil using rotary evaporation under a water aspirator vacuum. NMR, IR and Mass Spectral analyses confirm that the major product isolated by GLC trapping has the structure: ##STR32## Into a 25 ml round bottom flask equpped with magnetic stirrer thermometer, reflux condenser heating mantle while maintaining the temperature at 25° C-30° C The reaction mass is stirred for a period of 10 minutes is then added to the reaction mass with stirring at 25° C The reaction mass is heated to reflux (50° C-60° C) maintained at this temperature with stirring for a period of 4 hours with stirring is added with stirring The mass is then transferred to a separatory funnel the organic and aqueous phases are separated The aqueous phase is diluted with 5 ml water extracted with 7 ml of n-hexne washed with 5 ml saturated sodium chloride dried over anhydrous sodium sulfate, and gravity filtered The resulting solution is then concentrated to an amber oil evaporation under a water isolated by GLC trapping

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 25 ml round bottom flask equipped with magnetic stirrer, thermometer, water bath, and reflux condenser is added a solution containing 0.27 g of sodium methoxide (0.005 moles) in 3 ml. absolute methanol. While maintaining the solution at 25° C-30° C, 0.57 g (0.005 moles) of 2-methyl-3-furan thiol in 2 ml of absolute methanol is added thereto. At 25° C, 0.483 g (0.005 moles) of chloromethyl methyl sulfide having the formula: Into a 25 ml round bottom flask equipped with magnetic stirrer thermometer, water bath, and reflux condenser is added a solution While maintaining the solution at 25° C-30° C At 25° C

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 0.57 Grams (0.0050 moles) of 2-methyl-3-furanthiol and 1.32 grams (0.01 moles) of n-heptylmercaptan are dissolved in 12 ml of diethyl ether. 0.8 Grams (0.0075 moles) of sodium carbonate dissolved in 8 ml water is added to the reaction mass. Over a period of 20 minutes, a solution of 1.9 grams (0.0075 moles) of iodine dissolved in 6 ml diethyl ether is added to the reaction mass with stirring until the iodine color remains. The reaction mass is then stirred over a period of 35 minutes. is added to the reaction mass is added to the reaction mass