1-(3-Chlorophenyl)ethanone → (R)-1-(3-Chlorophenyl)ethanol

To a solution of borane-tetrahydrofuran (0.647 mL, 0.647 mmol, Aldrich, 1 M solution in THF) and (S)-MeCBS (0.647 mL, 0.647 mmol, Aldrich, 1M solution in toluene) was added simultaneously a solution of 3-chloroacetophenone (1.00 g, 6.47 mmol) in anhydrous tetrahydrofuran (2.42 mL) and a solution of borane-tetrahydrofuran (3.24 mL, 3.24 mmol, Aldrich, 1 M solution in THF) over 30 min at ambient temperature. After complete addition, the reaction mixture was stirred for 10 min, quenched slowly at 0° C. with methanol (0.94 mL) and then saturated HCl in ether (0.12 mL). After stirring at 0° C. for 5 min and ambient temperature for 30 min, the solution was concentrated in vacuo to an oil. The oil was twice diluted with benzene and concentrated in vacuo, diluted with ether, and concentrated in vacuo to an oil. The oil was purified by flash chromatography (silica gel, 20% EA in hexane) to give (R)-1-(3-chlorophenyl)ethanol as a clear colorless oil (0.784 g, 78%). Optical rotation in CHCl3 at 20° C. at concentration 0.220 was +40.90 (Literature, Bull. Chem. Soc. Jpn. 1996, 69(4), 1079-1085, optical rotation in CHCl3 at 21° C. at concentration 0.220 was +44°).

1. additionAfter complete addition
2. customquenched slowly at 0° C. with methanol (0.94 mL)
3. stirringAfter stirring at 0° C. for 5 min and ambient temperature for 30 min
4. concentrationthe solution was concentrated in vacuo to an oil
5. additionThe oil was twice diluted with benzene
6. concentrationconcentrated in vacuo
7. additiondiluted with ether
8. concentrationconcentrated in vacuo to an oil
9. customThe oil was purified by flash chromatography (silica gel, 20% EA in hexane)

ORD record

ord-ec0b778c499d43aa81a4d9e4863f9b25

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07888366B2