ethyl N-ethoxycarbonyliminocarbamate → 1,2-Bis(ethoxycarbonyl)-4-(4,8-dimethyl-3,7-nonadienyl)-1,2,3,6-tetrahydropyridazine

Participants

Reaction Conditions

Reaction Steps

A solution of the (E)-β-farnesene-containing product of Example 1 (14.5 g) in ether (20 ml) is cooled to -20° C. and diethyl azodicarboxylate (8.7 g) is slowly added with stirring. The mixture is stored at -20° C. overnight and then at 4° C., the reaction being shown by n.m.r. to be complete after 8 hours at 4° C. The mixture is then subjected to fractional distillation to give the adduct, 1,2-bis(ethoxycarbonyl)-4-(4,8-dimethyl-3,7-nonadienyl)-1,2,3,6-tetrahydropyridazine (I) as a yellow oil (8 g, 43%) 180°-185° C./0.3τ; nD20 1.4938; M+ (m/z as % of base peak): 378(2.9); δ(CCl4) 1.30 (t, 6H), 1.70 (m, 9H), 2.08 (m, 8H), 3.60-4.40 (m, 4H), 4.26 (q, 4H), 5.20 (m, 2H), 5.60 (br, t, 1H).

Provenance & Evidence