Sodium hydride → Ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrate

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% dispersion in mineral oil) (4.38 g) was added to an ice cold solution of ethyl 4-[1-(4-acetoxybenzoyl)indolizin-3-yl]butyrate (36.1 g) in a mixture of ethanol (200 ml) and tetrahydrofuran (200 ml). The mixture was stirred for 20 minutes at 0° C. and evaporated. The residual solution was poured into a mixture of diluted hydrochloric acid and ice, and extracted with a mixture of chloroform and methanol (10:1). The organic layer was washed with a sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate and evaporated. The residue was washed with ethyl acetate and diethyl ether to give ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrate as yellow powder (29.3 g).

Provenance & Evidence