Sodium hydride → methyl (E)-2-[2-(4-cyclopropylmethoxy-3,5-dichlorophenoxymethyl)phenyl]-3-methoxyacrylate

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Reaction Steps

A solution of 4-cyclopropylmethoxy-3,5-dichlorophenol (1.54 g; 6.6 mmoles) in DMF (5 ml) is added dropwise, at 0° C., to a suspension of sodium hydride (0.16 g; 6.6 mmoles) in N,N-dimethyl formamide (DMF; 5 ml). The mixture is kept under stirring at room temperature for 30 minutes and a solution of methyl (E)-2-(2bromomethylphenyl)-3-methoxyacrylate (1.9 g; 6.6 mmoles) in DMF (5 ml) is then added. The mixture is kept under stirring for 4 hours; the mixture is diluted with water (40 ml) and an extraction is effected with ethyl acetate (3×25 ml). The organic phases are joined, washed with water (2×20 ml), dried with sodium sulfate, filtered and concentrated at reduced pressure. The raw product obtained is purified by means of silica gel chromatography, eluting with hexane/ethyl acetate 9:1. 1.9 g of the desired product (thick oil) are obtained.

Provenance & Evidence