Benzeneacetic acid, 3,4-dimethoxy-, methyl ester → alpha-[5-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]pentyl]-3,4-dimethoxybenzeneacetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution, -78° C. under argon, of 2.38 g of 3,4-dimethoxyphenyl acetic acid methyl ester in 30 ml of tetrahydrofuran is added 12.45 ml of 1.0M sodium hexamethylsidilazide. The solution is stirred at -78° C. for 5 minutes and then warmed to 0° C. for 1 hour. To this solution is added 3.5 g of (5-bromopentyl)(1,1-dimethylethyl)dimethyl silane. The reaction mixture is allowed to warm to room temperature and stirred for 12 hours. The mixture is diluted with diethyl ether and water, the layers are separated and the organic layer is washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by chromatography (silica gel: hexane/ethyl acetate,5/1) to give 2.6 g of the desired product as a clear oil. MS(Hi res): calcd 410.2488 found 410.2492

Provenance & Evidence