Water → HCID 14722815, compound

Participants

Reaction Steps

A solution of 4-hydroxyphenylsulfonylacetone (5.7 g), 2-chlorobenzaldehyde (3.7 g), and ammonium acetate (50 mg) in toluene (50 ml) was heated at reflux using a Dean-Stark water separator for 2 hours. About 20 ml of the solvent was removed on a rotary evaporator. Methyl β-aminocrotonate (3.1 g) and methanol (40 ml) were then added to the remaining toluene solution. The resulting mixture was heated under nitrogen for 18 hours. The cooled reaction mixture was evaporated to dryness, and the residue was chromatographed on silica gel (elution with 1:3 to 1:2 ethyl acetate/hexane) to yield 4-(2-chlorophenyl)-3-(4-hydroxyphenyl)sulfonyl-5-methoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine, m.p. 223°-225° C.

Provenance & Evidence