Ethylamine → HCID 13366431, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2.0 g (5.3 mmol) of (2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(trifluoromethoxy)phenyl]-nonatetraenoic acid in 60 ml of dry THF and 1.6 g of (10 mmol) of carbonyldiimidazole was heated to 35°-40° C. for 0.5 hour. The reaction mixture was cooled to -10° C. and excess gaseous ethyl amine was introduced. The resulting mixture was stirred for 1 hour at 23° C., diluted with 100 ml of hexane, and filtered through silica gel (200 g, 1:1 ethyl acetate-hexane as elutant). Further chromatographic purification (silicia gel, 5 to 10% ethyl acetate in methylene chloride) gave a yellow solid which, after recrystallization (ethyl acetate-hexane), yielded 1.4 g of N-ethyl(2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(trifluoromethoxy)phenyl]-nonatetraenamide; mp 198°-200° C.

Provenance & Evidence