Benzyl Bromide → (2S,3S)-2-benzyl-3-hydroxy-gamma-butyrolactone

Temperature

-45 °C

Lithium hexamethyldisilazide (25 ml, 25 mmol) was loaded under argon gas in a reaction vessel. (S)-3-Hydroxy-γ-butyrolactone (1.012 g, 9.913 mmol) in THF (20 ml) was added thereto under cooling to −45° C. After stirring for 30 minutes at the same temperature, benzyl bromide (1.9 ml, 11.89 mmol) in THF (20 ml) was dropped thereto. After stirring for 4 hours at the same temperature, an aqueous saturated ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and condensed in vacuo. The residue was purified by silica gel chromatography to give (2S,3S)-2-benzyl-3-hydroxy-γ-butyrolactone (0.762 g, yield 40%).

1. additionwas dropped
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with water and saturated brine
4. dry with materialdried over magnesium sulfate, and condensed in vacuo
5. customThe residue was purified by silica gel chromatography

ORD record

ord-c3b982a85e4e4078ab696a10abcae5b3

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06268515B1