Butyl ether → 1-(4-Chlorophenyl)-2-methoxyethanone

Participants

Reaction Steps

Equipped with magnetic stirring, (methoxymethyl)-triphenylphosphonium chloride (5.2 g, 15.2 mmol) was suspended in anhydrous tetrahydrofuran at 0° C. under N2 flow. Phenyl lithium, in 1.8 M in di-n-butyl ether (8.4 mL, 15.2 mmol), was added such that the temperature did not exceed 4° C. Mixture remained at 0° C. for 15 minutes, and a solution of 4-chlorobenzonitrile (0.56 g, 4.07 mmol) dissolved in 10 mls of anhydrous tetrahydrofuran was added over 15 minutes. Reaction was warmed to room temperature and continued for another 2 hours. Reaction was quenched with 50 ml of water and mixture was extracted (3×100 mls) with ether. Combined ethers were washed (2×20 mls) brine, and dried over MgSO4. Organics were filtered and concentrated to an amber oil. Oil was loaded on a flash silica gel column and eluted with 10-40% EA/Hex gradient to afford 382 mg of 1-(4-chlorophenyl)-2-methoxy-ethanone. (51% yield).

Provenance & Evidence