Benzoyl chloride → (S)-beta-Benzoyloxy-gamma-butyrolactone

To the solution of (S)-β-Hydroxy-γ-butyrolactone (1.0 g, 9.8 mmol) in 25 mL pyridine was added dropwise BzCl (1.4 mL, 12.2 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred overnight. The reaction was concentrated and coevaporated with toluene two times in vacuo. The residue was partitioned between H2O (15 mL) and EtOAc (40 mL). The organic layer was washed with water and brine, and concentrated in vacuo. The residue was purified by chromatography on a silica gel column (n-hexane/EtOAc=8:1) to afford 101 (1.78 g, 8.6 mmol) as a white solid, in 89% yield, which was characterized as follows:

1. concentrationThe reaction was concentrated
2. customThe residue was partitioned between H2O (15 mL) and EtOAc (40 mL)
3. washThe organic layer was washed with water and brine
4. concentrationconcentrated in vacuo
5. customThe residue was purified by chromatography on a silica gel column (n-hexane/EtOAc=8:1)

ORD record

ord-41730e38b7e84917a0199cd983cacb83

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249177B2