Acetoacetic Acid → H-152/81

Participants

Reaction Conditions

Reaction Steps

A solution of 2,3-dichlorobenzaldehyde (0.70 g), 3-nitrooxy-2,2-bis(nitrooxymethyl)propyl ester of acetoacetic acid (1.42 g) and methyl 3-amino-crotonate (0.46 g) in tert-butyl alcohol (3 ml) was refluxed for 4.5 hours. The resulting mixture was cooled to 25° C. and then concentrated under reduced pressure. The residue obtained was subjected to column chromatography on silica gel (60 g) and eluted with a mixture of chloroform and methanol (100:1 by volume). The fractions containing the desired compound were collected and evaporated under reduced pressure. The residue obtained was recrystallized from a mixture of diethyl ether and diisopropyl ether to give 3-nitrooxy-2,2-bis(nitrooxymethyl)propyl ester of 4-(2,3-dichlorophenyl)-5-methoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid (1.11 g), mp 115° to 117.5° C.

Provenance & Evidence