4-Chlorobenzoyl chloride → HCID 53927902, compound

Participants

Reaction Steps

A solution of ethyl 5-(5-methoxyindol-2-yl)-2,4-pentadienoate (0.8 g, 2.9 mmol) in 20 ml of tetrahydrofuran (THF) was added dropwise to a suspension of sodium hydride (0.024 g of a 60% reagent) at 0° C. (ice bath). After addition, the mixture was stirred in the ice bath for 1 hour and a solution of p-chlorobenzoyl chloride (0.54 g) in 10 ml of THF was added; the resulting mixture was filtered to remove the precipitate and the filtrate was washed with brine, dried (magnesium sulfate) and concentrated on rotary evaporator to give a yellow oil. Crystallization of this oily substance from acetone-ether afforded 0.75 g of ethyl 5-(1-p-chlorobenzoyl-5-methoxyindol-2-yl)-2,4-pentadienoate as yellow powders, m.p., 121°-125° C. MS(EI): 40 g(M+), 336 (M+ --CO2Et).

Provenance & Evidence