p-METHYLACETOPHENONE → HCID 23017953, compound

Participants

Reaction Steps

Under an atmosphere of argon, a solution of 473 mg (1.44 mmol) of 4-(4-methanesulfonylphenoxymethyl)-2-methylquinoline in tetrahydrofuran was cooled to −78° C. and then, 1.44 mL (1.44 mmol) of 2 M lithium diisopropylamide was added thereto and stirred for 40 minutes. Into this solution was dropped a solution of 194 mg (1.59 mmol) of p-methylacetophenone in tetrahydrofuran, followed by stirring for 2.5 hours. The reaction was stopped by the addition of saturated brine, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered, and the filtrate was concentrated under a reduced pressure. The obtained residue was purified by column chromatography on silica gel (developing solvent; hexane:ethyl acetate=1:1 to 1:2) to obtain 440 mg (0.95 mmol) of 1-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl]-2-p-tolylpropan-2-ol (VIII-57). Its physical property is shown below.

Provenance & Evidence