Formic Acid → (1S)-1-(3-CHLOROPHENYL)ETHANOL

HRID 1751901Notes

Reaction equation

HRID 1751901 reaction equation
C([O-])=O.[K+].C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:15](=[O:17])[CH3:16])[CH:12]=[CH:13][CH:14]=1>[Ru].CO>[Cl:8][C:9]1[CH:10]=[C:11]([C@@H:15]([OH:17])[CH3:16])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 149331-(3-Chlorophenyl)ethanoneHCID 2735122Potassium Formate

Product 1

HCID 6950741(1S)-1-(3-CHLOROPHENYL)ETHANOLYield 85%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A ruthenium complex RuCl[(S,S)-BnSO2dpen] (mesitylene) (1.2 mg, 0.002 mmol), potassium formate (1.0 g, 12 mmol), formic acid (138 mg, 3 mmol) and 3′-chloroacetophenone (1.55 g, 10 mmol, substrate/catalyst ratio=5000) were set in a 20 mL glass Schlenk-type reaction tube under an argon atmosphere. Methanol (6 mL) was added thereto and stirred at 50° C. for 24 hours to give (S)-1-(3′-chlorophenyl)ethanol at 85% yield and 96.5% ee optical purity.

Sources & evidence

ORD record
ord-e2f8906ca9834eb784e10ff339a7cbcd
Source dataset
uspto-grants-2015_10
Patent number
US09162934B2

Reaction notes

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