Ethyl Acetate → HCID 10018093, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(3-hydroxyphenyl)-5-(4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde oxime (0.76 g, 2.3 mmol) and pyridinium hydrochloride (2.7 g, 23 mmol) was heated at 195-205° C. in a 200 mL round bottom flask fitted with a 250 mL bump trap. After 2 h, the reaction mixture was cooled to 23° C. and taken up in a minimum of ethyl acetate (100 mL). The organic phase was washed with water (2×50 mL), saturated aqueous NaHCO3 (50 mL) and brine (50 mL), dried (Na2SO4) and concentrated in vacuo to give the crude product as a brown solid (0.61 g) which was pre-adsorbed on silica gel (2 g). Flash chromatography (10 g silica gradient 20%-30%-40% ethyl acetate-hexane) gave the title compound (0.37 g, 52%, m.p. 220-22° C.) as a pale orange solid after recrystallization from hot ethyl acetate-hexane.

Provenance & Evidence