4-[2-[5,6-Dihydro-5,5-dimethyl-8-[[(trifluoromethyl)sulfonyl]oxy]-2-naphthalenyl]ethynyl]benzoic acid ethyl ester → AGN 193109 Ethyl Ester

Participants

Reaction Steps

Employing the same general procedure as for the preparation of ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(2-thiazolyl)naphth-3-yl)ethynyl]benzoate (Compound 67), 200.0 mg (0.42 mmol) of ethyl 4-[(5-triflouromethylsulfonyloxy-7,8-dihydro-8,8-dimethylnaphth-3-yl)ethynyl]benzoate (Compound 66) was converted into the title compound (colorless solid) using 113.8 mg (0.835 mmol) of zinc chloride and 4-methylphenyllithium (prepared by adding 40.4 mg (0.42 ml, 0.63 mmol) of n-butyllithium (1.5 M solution in hexane) to a cold solution (−78° C.) of 108.0 mg (0.63 mmol) of 4-bromotoluene in 1.0 ml of THF).

Provenance & Evidence