1-(3,5-Bis(trifluoromethyl)phenyl)ethan-1-one → (alphaS)-alpha-Methyl-3,5-bis(trifluoromethyl)benzenemethanol

HRID 1751902Notes

Reaction equation

HRID 1751902 reaction equation
C([O-])=O.[K+].[F:5][C:6]([F:21])([F:20])[C:7]1[CH:8]=[C:9]([C:17](=[O:19])[CH3:18])[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1>[Ru].CO>[F:5][C:6]([F:20])([F:21])[C:7]1[CH:8]=[C:9]([C@@H:17]([OH:19])[CH3:18])[CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1

Participants

5

Reactant 2

HCID 1216161-(3,5-Bis(trifluoromethyl)phenyl)ethan-1-oneHCID 2735122Potassium Formate

Product 1

HCID 9816575(alphaS)-alpha-Methyl-3,5-bis(trifluoromethyl)benzenemethanolYield 100%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A ruthenium complex Ru(OTf)[(S,S)-iso-BuSO2dpen] (p-cymene) (1.4 mg, 0.002 mmol), potassium formate (1.0 g, 12 mmol), and 3′,5′-bis(trifluoromethyl)acetophenone (2.56 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′,5′-bis(trifluoromethyl)phenyl]ethanol at 100% yield and 87.7% ee optical purity.

Sources & evidence

ORD record
ord-1cb5db4b9ce7442c9ebc7d7dd8c4b818
Source dataset
uspto-grants-2015_10
Patent number
US09162934B2

Reaction notes

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