ethyl 2-(oxan-4-yl)acetate

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:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1 g (tetrahydro-pyran-4-yl)-acetic acid ethyl ester [103260-44-2] in 3 ml of dry tetrahydrofuran is added dropwise to a solution of lithium diisopropyl amide (freshly prepared from 1 ml diisopropyl amine and 4.3 ml 1.6 M butyllithium solution in hexanes) in 5 ml of dry tetrahydrofuran at −78° C. The reaction mixture is stirred for 15 minutes at −78° C. and then 0.46 ml of methyl iodide are added and the mixture is allowed to warm to 0° C. over a period of 15 minutes. The reaction mixture is re-cooled to −78° C. and then a solution of lithium diisopropyl amide (freshly prepared from 1 ml diisopropyl amine and 4.3 ml 1.6 M butyllithium solution in hexanes) in 5 ml of dry tetrahydrofuran is added dropwise. The solution is stirred for 15 minutes at −78° C. and then 0.46 ml of methyl iodide are added and the mixture is allowed to warm to room temperature. After 2 hours, the reaction mixture is quenched with 20 ml of 1M HCl and then extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.27 (1:5 EtOAc-heptane). to warm to 0° C. over a period of 15 minutes The reaction mixture is re-cooled to −78° C. is added dropwise The solution is stirred for 15 minutes at −78° C. to warm to room temperature After 2 hours the reaction mixture is quenched with 20 ml of 1M HCl extracted with tert-butyl methyl ether (2×) The combined organic phases are washed with brine dried over sodium sulphate concentrated by evaporation

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1 g (tetrahydro-pyran-4-yl)-acetic acid ethyl ester [103260-44-2] in 3 ml of dry tetrahydrofuran is added dropwise to a solution of lithium diisopropyl amide (freshly prepared from 1 ml diisopropyl amine and 4.3 ml 1.6 M butyllithium solution in hexanes) in 5 ml of dry tetrahydrofuran at −78° C. The reaction mixture is stirred for 15 minutes at −78° C. and then 0.46 ml of methyl iodide are added and the mixture is allowed to warm to 0° C. over a period of 15 minutes. The reaction mixture is re-cooled to −78° C. and then a solution of lithium diisopropyl amide (freshly prepared from 1 ml diisopropyl amine and 4.3 ml 1.6 M butyllithium solution in hexanes) in 5 ml of dry tetrahydrofuran is added dropwise. The solution is stirred for 15 minutes at −78° C. and then 0.46 ml of methyl iodide are added and the mixture is allowed to warm to room temperature. After 2 hours, the reaction mixture is quenched with 20 ml of 1M HCl and then extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.27 (1:5 EtOAc-heptane). to warm to 0° C. over a period of 15 minutes The reaction mixture is re-cooled to −78° C. is added dropwise The solution is stirred for 15 minutes at −78° C. to warm to room temperature After 2 hours the reaction mixture is quenched with 20 ml of 1M HCl extracted with tert-butyl methyl ether (2×) The combined organic phases are washed with brine dried over sodium sulphate concentrated by evaporation

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture composed of ethyl 2-(2H-pyran-4(3H,5H,6H)-ylidene)acetate (10 g, 58.75 mmol) and ammonium formate (37 g, 587.54 mmol) in methanol (150 ml) was added 10% Pd-carbon (1.0 g) at room temperature, and the mixture was stirred at 70° C. for 15 hr. The reaction mixture was allowed to cool to room temperature, and the catalyst was collected by filtration through Celite pad and was washed with methanol. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate=94:6) to give the title compound as an oil (7.9 g, yield 78%). to cool to room temperature the catalyst was collected by filtration through Celite pad was washed with methanol The filtrate was concentrated under reduced pressure the residue was chromatographed on silica gel column (hexane:ethyl acetate=94:6)

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1 g (tetrahydro-pyran-4-yl)-acetic acid ethyl ester [103260-44-2] in 3 ml of dry tetrahydrofuran is added dropwise to a solution of lithium diisopropyl amide (freshly prepared from 1 ml diisopropyl amine and 4.3 ml 1.6 M butyllithium solution in hexanes) in 5 ml of dry tetrahydrofuran at −78° C. The reaction mixture is stirred for 15 minutes at −78° C. and then 0.46 ml of methyl iodide are added and the mixture is allowed to warm to 0° C. over a period of 15 minutes. The reaction mixture is re-cooled to −78° C. and then a solution of lithium diisopropyl amide (freshly prepared from 1 ml diisopropyl amine and 4.3 ml 1.6 M butyllithium solution in hexanes) in 5 ml of dry tetrahydrofuran is added dropwise. The solution is stirred for 15 minutes at −78° C. and then 0.46 ml of methyl iodide are added and the mixture is allowed to warm to room temperature. After 2 hours, the reaction mixture is quenched with 20 ml of 1M HCl and then extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.27 (1:5 EtOAc-heptane). to warm to 0° C. over a period of 15 minutes The reaction mixture is re-cooled to −78° C. is added dropwise The solution is stirred for 15 minutes at −78° C. to warm to room temperature After 2 hours the reaction mixture is quenched with 20 ml of 1M HCl extracted with tert-butyl methyl ether (2×) The combined organic phases are washed with brine dried over sodium sulphate concentrated by evaporation

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

実験手順: To 15 mL of tetrahydrofuran (THF) at 0° C. was added LiAlH4 (0.28 g, 7.3 mmol). This mixture was stirred for 10 min then the ethyl tetrahydropyran-4-yl-acetate (Combi-Blocks Inc., 0.50 g, 2.9 mmol) was added. The reaction was stirred for 5 min at 0° C. then was allowed to warm to ambient temperature and was stirred for 90 min. The reaction was quenched with excess NaHSO4.10H2O and was stirred for 60 min. The mixture was filtered through Celite. The filtrate was concentrated to give the title compound which was carried on without further purification. MS (DCI/NH3) m/z 131 (M+H)+. The reaction was stirred for 5 min at 0° C. was stirred for 90 min The reaction was quenched with excess NaHSO4.10H2O was stirred for 60 min The mixture was filtered through Celite The filtrate was concentrated

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

実験手順: 20 ml of methanol, 10 ml of water and 1 g of sodium hydroxide were added to 0.9 g of ethyl 4-tetrahydropyranylacetate and agitated at 80° C. for 1 hour. The solvent was removed by distillation, to which water was added. After washing with ethyl acetate, a hydrochloric acid aqueous solution was added to the resultant aqueous phase to an extent of pH of 3, followed by extraction with chloroform under salting-out conditions and drying with anhydrous magnesium sulfate. This was removed by filtration and the solvent was distilled off, thereby obtaining 0.87 g of a crude intended compound. The solvent was removed by distillation, to which water was added After washing with ethyl acetate a hydrochloric acid aqueous solution was added to the resultant aqueous phase to an extent of pH of 3 followed by extraction with chloroform under salting-out conditions drying with anhydrous magnesium sulfate This was removed by filtration the solvent was distilled off obtaining 0.87 g of a crude intended compound

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

実験手順: To 15 mL of tetrahydrofuran (THF) at 0° C. was added LiAlH4 (0.28 g, 7.3 mmol). This mixture was stirred for 10 min then the ethyl tetrahydropyran-4-yl-acetate (Combi-Blocks Inc., 0.50 g, 2.9 mmol) was added. The reaction was stirred for 5 min at 0° C. then was allowed to warm to ambient temperature and was stirred for 90 min. The reaction was quenched with excess NaHSO4.10H2O and was stirred for 60 min. The mixture was filtered through Celite. The filtrate was concentrated to give the title compound which was carried on without further purification. MS (DCI/NH3) m/z 131 (M+H)+. The reaction was stirred for 5 min at 0° C. was stirred for 90 min The reaction was quenched with excess NaHSO4.10H2O was stirred for 60 min The mixture was filtered through Celite The filtrate was concentrated

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: 20 ml of methanol, 10 ml of water and 1 g of sodium hydroxide were added to 0.9 g of ethyl 4-tetrahydropyranylacetate and agitated at 80° C. for 1 hour. The solvent was removed by distillation, to which water was added. After washing with ethyl acetate, a hydrochloric acid aqueous solution was added to the resultant aqueous phase to an extent of pH of 3, followed by extraction with chloroform under salting-out conditions and drying with anhydrous magnesium sulfate. This was removed by filtration and the solvent was distilled off, thereby obtaining 0.87 g of a crude intended compound. The solvent was removed by distillation, to which water was added After washing with ethyl acetate a hydrochloric acid aqueous solution was added to the resultant aqueous phase to an extent of pH of 3 followed by extraction with chloroform under salting-out conditions drying with anhydrous magnesium sulfate This was removed by filtration the solvent was distilled off obtaining 0.87 g of a crude intended compound