2-Chloroacetophenone → 2-Chloro-1-phenylethanol, (+)-

HRID 2180331Notes

Reaction equation

HRID 2180331 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C(O)=O.C(N(CC)CC)C>C(OCC)(=O)C.C1(C)C=CC(S(N[C@H](C2C=CC=CC=2)[C@@H](C2C=CC=CC=2)N)(=O)=O)=CC=1.Cl[Rh+]C1(C)C(C)=C(C)C(C)=C1C>[Cl:1][CH2:2][C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4]

Participants

5

Reactant 2

HCID 107572-ChloroacetophenoneHCID 11084032Triethylammonium formate

Product 1

HCID 6433232-Chloro-1-phenylethanol, (+)-Yield 93%

Reagents, catalysts & solvents 2

HCID 178425932HCID 178425932, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloroacetophenone (154.0 mg, 1.0 mmol) and a formic acid/triethylamine azeotropic mixture (0.2 ml) were added to a solution of chloro(pentamethylcyclopentadienyl)rhodium (III) (1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (0.67 mg, 0.001 mmol, s/c=1000) in ethyl acetate (1.0 ml), followed by stirring at room temperature for 2 hours. After completion of the reaction, purification by silica gel column chromatography furnished a desired compound, (S)-(+)-2-chloro-1-phenylethanol (145.1 mg; yield: 93.0%; optical purity: 96.6% ee).

Workup

  1. customAfter completion of the reaction, purification by silica gel column chromatography

Sources & evidence

ORD record
ord-43bf0da797804f4fad9671722faf80cf
Source dataset
uspto-grants-2005_05
Patent number
US06888012B2

Reaction notes

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