1-Chloro-4-(chloromethyl)benzene → methyl (RS)-5-[3-(4-chlorobenzyloxy)phenyl]-4-(2-methylphenyl)-5-oxopentanoate

Participants

Reaction Conditions

Reaction Steps

A stirred solution of methyl (RS)-5-[3-(hydroxy)phenyl]-4-(2-methylphenyl)-5-oxo-pentanoate (1.68 g) in dimethylformamide (20 mL) is treated with 60% sodium hydride in oil (237 mg). After 15 minutes the mixture is treated with 4-chlorobenzyl chloride (953 mg) and heated at 60° C. for 1 hour. The reaction mixture is evaporated, the residue is dissolved in diethyl ether, washed with water, dried, and evaporated, to give methyl (RS)-5-[3-(4-chlorobenzyloxy)phenyl]-4-(2-methylphenyl)-5-oxopentanoate (2.05 g), in the form of a colouriess oil. [NMR(CDCl3):- 2.0-2.5(4H,m),2.5(3H,s), 3.65(3H,s), 4.8(1H,m),5.0(2H,q),7.0-7.5(12H)].

Provenance & Evidence