tridecanoic acid

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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: To a benzene solution containing 5.0 g (0.023 mol) of tridecanoic acid was added 25 g of thionyl chloride, followed by refluxing for 5 hours. The excess of thionyl chloride and benzene were removed by distillation to obtain tridecanoyl chloride. by refluxing for 5 hours The excess of thionyl chloride and benzene were removed by distillation

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

実験手順: Following a procedure similar to that described in Example 12, but using 400 mg of radicicol, 588 mg of tridecanoic acid, 6 ml of dry tetrahydrofuran, 566 mg of dicyclohexylcarbodiimide and a catalytic amount of dimethylaminopyridine, 688 mg of the title compound were obtained.

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

実験手順: Following a procedure similar to that described in Example 12, but using 400 mg of radicicol, 588 mg of tridecanoic acid, 6 ml of dry tetrahydrofuran, 566 mg of dicyclohexylcarbodiimide and a catalytic amount of dimethylaminopyridine, 688 mg of the title compound were obtained.

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

実験手順: Following a procedure similar to that described in Example 12, but using 400 mg of radicicol, 588 mg of tridecanoic acid, 6 ml of dry tetrahydrofuran, 566 mg of dicyclohexylcarbodiimide and a catalytic amount of dimethylaminopyridine, 688 mg of the title compound were obtained.

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

実験手順: Tridecanoic acid (102.8 g, 0.48 mol) was dissolved into 480 ml of methylene chloride, and 52.6 ml (0.72 mol) of thionyl chloride and 0.2 ml of N,N-dimethylformamide were added thereto. The mixture was allowed to stand overnight followed by concentration under reduced pressure, and the remaining oil was added to 400 ml of methylene chloride containing 106.6 g (0.8 mol) of anhydrous aluminium chloride. A solution of 50.05 g (0.4 mol) of methyl pyrrole-2-carboxylate in 200 ml of methylene chloride was added dropwise to the mixture for ca. 40 minutes at 3° to 9° C. After the addition was finished, the temperature was raised gradually to room temperature, and the mixture was stirred for 2 hours followed by pouring it into 800 ml of ice water. To this mixture was added 1000 ml of methylene chloride to completely dissolve the crystals. The organic layer was separated, washed with water three times and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was recrystallized from 400 ml of ethyl acetate and 400 ml of hexane to give 107.2 g (83% yield) of methyl 4-tridecanoylpyrrole-2-carboxylate as white crystals, m.p. 92°-93° C. were added followed by concentration under reduced pressure After the addition to completely dissolve the crystals The organic layer was separated washed with water three times dried over anhydrous magnesium sulfate After concentration under reduced pressure the residue was recrystallized from 400 ml of ethyl acetate and 400 ml of hexane

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

実験手順: To a solution (20 ml) of 2.78 g (20 mmol) of ethyl pyrrole-3-carboxylate in benzene was added tridecanoyl chloride prepared from 4.28 g (20 mml) of tridecanoic acid in a conventional manner, followed by further dropwise addition of 3.5 ml (30 mmol) of stannic chloride. After the addition, the mixture was stirred for 15 hours at room temperature, treated with diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the residue was purified by subjecting it to silica gel column chromatography (eluent: ethyl acetate/hexane=1/7) to obtain 4.85 g (72% yield) of ethyl 5-tridecanoylpyrrole-3-carboxylate. After the addition extracted with ethyl acetate The extract was washed with water dried over anhydrous magnesium sulfate After removing the solvent under reduced pressure the residue was purified

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a one L (liter) two-necked flask were placed 158.7 g (0.74 mol) of tridecanoic acid and 200 milliliter (mL) of cyclohexane, and the flask was equipped with a 100 mL dropping funnel containing 83.3 g (0.7 mol) of thionyl chloride and a reflux tube. Then, the tridecanoic acid was completely dissolved under heating and stirring of the flask in an oil bath at 80° C. Thereafter the thionyl chloride was added dropwise over a period of 2 hours, and further the oil bath was maintained at 80° C. for one hour. From the resultant reaction solution were removed the cyclohexane and the thionyl chloride under reduced pressure by means of an aspirator. The resultant reaction mixture was subjected to vacuum distillation. Thus 166.0 g (0.71 mol) of tridecanoyl chloride was obtained in a yield of 95.9% based on the fed tridecanoic acid. the flask was equipped with a 100 mL under heating further the oil bath was maintained at 80° C. for one hour From the resultant reaction solution were removed the cyclohexane The resultant reaction mixture was subjected to vacuum distillation

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a one L (liter) two-necked flask were placed 158.7 g (0.74 mol) of tridecanoic acid and 200 milliliter (mL) of cyclohexane, and the flask was equipped with a 100 mL dropping funnel containing 83.3 g (0.7 mol) of thionyl chloride and a reflux tube. Then, the tridecanoic acid was completely dissolved under heating and stirring of the flask in an oil bath at 80° C. Thereafter the thionyl chloride was added dropwise over a period of 2 hours, and further the oil bath was maintained at 80° C. for one hour. From the resultant reaction solution were removed the cyclohexane and the thionyl chloride under reduced pressure by means of an aspirator. The resultant reaction mixture was subjected to vacuum distillation. Thus 166.0 g (0.71 mol) of tridecanoyl chloride was obtained in a yield of 95.9% based on the fed tridecanoic acid. the flask was equipped with a 100 mL under heating further the oil bath was maintained at 80° C. for one hour From the resultant reaction solution were removed the cyclohexane The resultant reaction mixture was subjected to vacuum distillation

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

実験手順: A solution of n-tridecanoic acid (Sigma Chemical Co.) (12.5 g), 2,4,5-trichlorophenol (11.5 g), and N,N'-dicyclohexylcarbodiimide (12.0 g) in methylene chloride (650 ml) is stirred at room temperature for 16 hours. The reaction mixture is then filtered and dried in vacuo to give 2,4,5-trichlorophenyl n-tridecanoate (22 g). The material is purified by column chromatography over silica gel (Woelm) using toluene as the eluent. Fractions are monitored by TLC using a shortwave UV light for detection. Fractions containing the purified product are pooled and concentrated in vacuo to dryness. The reaction mixture is then filtered dried in vacuo