gamma-Heptalactone → HCID 23154592, compound

Temperature

-70 °C

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.

1. customThe reaction solution was quenched with methanol (3.0 ml) at −70° C.
2. waitleft to room temperature
3. additionAfter adding a 10% aqueous solution of citric acid
4. stirringthis reaction solution was stirred for 5 minutes
5. extractionThen this solution was extracted with ethyl acetate
6. washthe organic layer was washed with a brine
7. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
8. customthe solvent was evaporated
9. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→80:20)

ORD record

ord-54bfdfcece78493b9b20290b87d15444

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678810B2