HCID 15132272, compound → HCID 15132273, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4.4 g (13.1 mmole) of ethyl 3-phenyl-4-(4-trifluoromethylphenyl)butanoate dissolved in 50 ml of tetrahydrofuran was added dropwise over a ten minute period to a 250 ml flask containing a 0° C. mixture of lithium aluminum hydride (745 mg, 19.6 mmole) in 50 ml of tetrahydrofuran. The resulting mixture was warmed to room temperature (22° C.), stirred at that temperature for about 2 hours, cooled to 0° C. again, and quenched by adding approximately 25 ml of water dropwise over a five minute period. The reaction mixture was acidified to a pH of about 1.0 using 6N hydrochloric acid and extracted with ethyl acetate. The organic extracts were combined, washed with water and a saturated brine solution, and finally dried over anhydrous sodium sulfate. The volatiles were removed under reduced pressure to provide 3.66 g of 3-phenyl-4-(4-trifluoromethylphenyl)butanol as a colorless oil. The compound was identified by N.M.R. analysis employing a 300 mHz instrument in CDCl3 ; δ=1.92 (multiplet, 2H); 2.97 (multiplet, 3H); 3.43 and 3.52 (multiplet, 2H); 7.08-7.53 (multiplet, 9H).

Provenance & Evidence