5-propyloxolan-2-one

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.02M solution of diisobutylalminium hydride in toluene (23.4 ml) was added dropwise to a solution of 5-propyldihydrofuran-2-one (1.50 g) in toluene (30 ml) over 50 minutes at −70° C. under nitrogen atmosphere, and the mixture was stirred for 1 hour at −70° C. The reaction solution was quenched with methanol (3.0 ml) at −70° C., and then left to room temperature. After adding a 10% aqueous solution of citric acid, this reaction solution was stirred for 5 minutes. Then this solution was extracted with ethyl acetate, and the organic layer was washed with a brine. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated, and then the residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→80:20) to yield 5-propyltetrahydrofuran-2-ol (440 mg) as a colorless oil. The reaction solution was quenched with methanol (3.0 ml) at −70° C. left to room temperature After adding a 10% aqueous solution of citric acid this reaction solution was stirred for 5 minutes Then this solution was extracted with ethyl acetate the organic layer was washed with a brine After the organic layer was dried over anhydrous magnesium sulfate the solvent was evaporated the residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→80:20)

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.02M solution of diisobutylalminium hydride in toluene (23.4 ml) was added dropwise to a solution of 5-propyldihydrofuran-2-one (1.50 g) in toluene (30 ml) over 50 minutes at −70° C. under nitrogen atmosphere, and the mixture was stirred for 1 hour at −70° C. The reaction solution was quenched with methanol (3.0 ml) at −70° C., and then left to room temperature. After adding a 10% aqueous solution of citric acid, this reaction solution was stirred for 5 minutes. Then this solution was extracted with ethyl acetate, and the organic layer was washed with a brine. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated, and then the residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→80:20) to yield 5-propyltetrahydrofuran-2-ol (440 mg) as a colorless oil. The reaction solution was quenched with methanol (3.0 ml) at −70° C. left to room temperature After adding a 10% aqueous solution of citric acid this reaction solution was stirred for 5 minutes Then this solution was extracted with ethyl acetate the organic layer was washed with a brine After the organic layer was dried over anhydrous magnesium sulfate the solvent was evaporated the residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→80:20)