Potassium Carbonate → Ethyl 2-Methyl-2-{4-[2-methoxy-5-chloro-benzamido-methyl]-biphenyl-4'-oxy}-propionate

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Reaction Steps

2.7 gm (7.35 millimols) of 4-[2-methoxy-5-chlorobenzamido-methyl]-4'-hydroxy-biphenyl were refluxed in 30 ml of methyl ethyl ketone with 1.26 gm (9.2 millimols) of potassium carbonate for 1 to 2 hours, and then 2.23 gm (11 millimols) of ethyl 2-bromo-2-methyl-propionate were added dropwise. After three hours, another 0.63 gm (4.6 millimols) of potassium carbonate and 0.46 gm (2.2 millimols) of 2-bromo-2-methyl-propionate were added to complete the reaction, and the mixture was heated for 3 to 4 hours more. After cooling, filtering and distilling off the solvent, the residual crude product was purified by chromatography on a silicagel column with benzene/ethyl acetate (9:1) as the eluant. The evaluation of column chromatograph was carried out by thin-layer chromatography. The fractions containing the pure product were combined, and the solvent was distilled off, yielding 1.8 gm (51% of theory) of a slightly yellow oil. M.p. < 20° C.

Provenance & Evidence