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ChemicalBook CAS DataBase List (S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol
225920-05-8

(S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol synthesis

2synthesis methods
3',5'-Bis(trifluoromethyl)acetophenone

30071-93-3

(S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol

225920-05-8

General procedure: under argon protection, the 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 to catalyst ratio 5000:1) were added to a 20 mL glass Schlenk reaction tube. Subsequently, methanol (6 mL) was added and the reaction was stirred at 50 °C for 24 hours. Upon completion of the reaction, (S)-1-[3,5-bis(trifluoromethyl)phenyl]ethanol was obtained in 100% yield with an enantiomeric excess (ee) value of 87.7%.

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Yield:225920-05-8 100%

Reaction Conditions:

with potassium formate;Ru(OTf)[(S,S)-iso-BuSO2dpen](p-cymene) in methanol at 50; for 24 h;Inert atmosphere;

Steps:

23
Working Example 23; 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.

References:

Kanto Kagaku Kabushiki Kaisha US2011/282077, 2011, A1 Location in patent:Page/Page column 8

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