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-7e29da1f29b94645bdad163192ea4989

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076310B2