Sodium hydride → Ethyl 2-[1-(3-butoxy-4-iodophenyl)meth-(e)-ylidene]butyrate

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Reaction Steps

A solution of 9 mL (37.8 mmol) of triethyl 2-phosphonobutyrate in 20 mL of tetrahydrofuran is added to a mixture of 1.52 g (37.8 mmol) of sodium hydride in 15 mL of tetrahydrofuran. The reaction medium is stirred for 20 minutes. A solution of 3.83 g (12.6 mmol) of 3-butoxy-4-iodobenzaldehyde (prepared as described in Example 19g) in 15 mL of tetrahydrofuran is then added to the reaction mixture and the reaction medium is stirred at room temperature for 2 hours 30 minutes. The reaction medium is poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and dried over magnesium sulfate. The solvent is evaporated off and the residue (11.49 g) is purified by chromatography on silica gel eluted with a 95/5 heptane/ethyl acetate mixture. 4.90 g (97%) of ethyl 2-[1-(3-butoxy-4-iodophenyl)meth-(E)-ylidene]butyrate are obtained in the form of a yellow oil that crystallizes.

Provenance & Evidence