Sodium hydride → Ethyl 2-[1-(3'-methylaminobiphenyl-4-yl)meth-(e)-ylidene]pentanoate

Participants

Reaction Steps

197 mg (4.9 mmol) of sodium hydride are added to a mixture of 1.2 mL (4.9 mmol) of triethyl 2-phosphonopentanoate and 415 mg of 3′-methylaminobiphenyl-4-carbaldehyde prepared as described in Example 9b (2.0 mmol) in 10 mL of tetrahydrofuran. The reaction mixture is stirred at room temperature overnight. The reaction medium is poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over sodium sulfate. The solvent is evaporated off and the residue (1 g) is purified by chromatography on a column of silica eluted with a 90/10 heptane/ethyl acetate mixture. 511 mg (81%) of ethyl 2-[1-(3′-methylaminobiphenyl-4-yl)meth-(E)-ylidene]pentanoate are obtained in the form of a yellow oil.

Provenance & Evidence