Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (E)-ethyl 3-(3-(4-cyano-2-methylphenyl)-4-(4-methoxyphenyl)thiophen-2-yl)acrylate

Participants

Reaction Conditions

Reaction Steps

The mixture of compound 4-(2-formyl-4-(4-methoxyphenyl)thiophen-3-yl)-3-methylbenzonitrile (Scheme I, 4A, X1=4-methoxyphenyl, X2=4-cyano-2-methylphenyl) (0.16 g, 0.48 mmol) and (carbethoxymethylene)triphenylphosphorane (Ph3P═CHCOOEt) (0.17 g, 0.48 mmol) in toluene (15 mL) was heated to 100° C. for 14 h. After being cooled down to room temperature, the reaction mixture was concentrated and purified by silica gel column chromatography (petroleum ether/ethyl acetate=20:1) to afford (E)-ethyl 3-(3-(4-cyano-2-methylphenyl)-4-(4-methoxyphenyl)thiophen-2-yl)acrylate (Scheme I, 5A, X1=4-methoxyphenyl, X2=4-cyano-2-methylphenyl) (0.27 g, yield 100%) as a white solid.

Provenance & Evidence