Chlorotrimethylsilane → (R)-(+)-3-Chlorostyrene oxide

At about 0° C., trimethylsilyl chloride (3.7 g, 34.06 mmol, 1.5 equiv.) was added to a solution of (R)-1-(3-chlorophenyl)ethane-1,2-diol (4 g, 23.17 mmol, 1 equiv.) and triethyl orthoacetate (5.6 g, 34.52 mmol, 1.5 equiv.) in dichloromethane (20 mL). After stirring the solution for about 1 hour, the solvent was removed by evaporation. The resulting crude product was resuspended in dry methanol (20 mL) and then potassium carbonate (8 g, 57.88 mmol, 2.5 equiv.) was added. The suspension was stirred vigorously for about 2 hours, and then filtered. The resulting filtrate was washed with dichloromethane and then concentrated in vacuo. The resulting crude was purified by silica gel column chromatography (ethyl acetate:petroleum ether (1:15)) to obtain the title product as a colorless oil (2.2 g; yield=61%). 1H NMR (300 MHz, DMSO-d6) δ: 7.25-7.43 (m, 4H), 3.97 (m, 1H), 3.13 (m, 1H), 2.88 (m, 1H).

1. customthe solvent was removed by evaporation
2. stirringThe suspension was stirred vigorously for about 2 hours
3. filtrationfiltered
4. washThe resulting filtrate was washed with dichloromethane
5. concentrationconcentrated in vacuo
6. customThe resulting crude was purified by silica gel column chromatography (ethyl acetate:petroleum ether (1:15))

ORD record

ord-a747545dacfd49079911ab8672cfedb6

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778998B2