Ethanone, 1-(2-chlorophenyl)- → (1R)-1-(2-chlorophenyl)ethan-1-ol

HRID 2111007Notes

Reaction equation

HRID 2111007 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].B(Cl)([C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@@H](C2)C1)[C@@H]1[C@@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([OH:10])[CH3:9]

Participants

3

Reactant 2

HCID 72864Ethanone, 1-(2-chlorophenyl)-HCID 91873398(+)-b-Chlorodiisopinocamphenylborane

Product 1

HCID 6999092(1R)-1-(2-chlorophenyl)ethan-1-olYield 73.3%

Procedure

Reaction was carried out using 2′-chloroacetophenone (11.90 g, 76.77 mmol) and (+)-B-chlorodiisopinocamphenylborane ((+)-DIP-C1) (25.00 g, 77.88 mmol) and according to J. Org. Chem., 1985, vol. 50, p. 5446; and 1988, vol. 53, p. 2916, to give the title compound (8.81 g, 72%). The optical purity was determined by HPLC analysis using an optically active column after conversion to the acetate (using acetic anhydride and triethylamine in dichloromethane).

Workup

  1. customReaction

Sources & evidence

ORD record
ord-759029748a754e1a80c65d045cb79a19
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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