Iodine → (E,E)-N-(2-Methylpropyl)-2,4-decadienamide

Participants

Reaction Steps

277 mg of 2E,4Z-decadienoic acid-N-isobutylamide from Example 1 were stirred with 29 mg of iodine in 10 ml of toluene for one hour at room temperature. The mixture was chromatographed on silica gel 60 with the eluent hexane/ethyl acetate 5:1. Yield: 61 mg (>95%, NMR); 1H-NMR (CDCl3; 200 MHz): 7.19 (1H, dd, 14.9 Hz, 9.7 Hz), 6.13 (1H, dd, 15.1 Hz, 9.6 Hz), 6.07 (1H, dd, 15.1 Hz, 6.4 Hz), 5.75 (1H, d 14.9 Hz), 5.50 (1H, bs), 3.17 (2H, dd, 6.9 Hz, 6.1 Hz), 2.14 (2H, dd, 7 Hz, 6.4 Hz), 1.80 (1H, m, 6.7 Hz), 1.42 (2H, m, 7.1 Hz), 1.37-1.22 (4H, m), 0.93 (6H, d, 6.7 Hz), 0.89 (3H, m) ppm.

Provenance & Evidence