Water → HCID 25010671, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl (2E,4E,8Z,11Z,14Z,17Z)-2-methyl-icosa-2,4,8,11,14,17-hexaenoate (10) in methanol was added an aqueous solution of KOH (8 equiv.) and the mixture was heated to 60-70° C. for 2 hrs. The solution was cooled, water was added and the mixture acidified. The mixture was then extracted with ethyl acetate. The combined organic phases were washed with water and dried (MgSO4). Evaporation of the solvents under reduced pressure followed by flash chromatography on silica gel (8:2 hexane-EtOAc) gave the acid 11. δH(300 MHz): 0.96 (t, J 7.5, 3H, CH3), 1.91 (d, J 0.75, 3H, CH3), 2.08 (m, 2H), 2.2-2.4 (m, 4H), 2.7-2.9 (m, 6H), 5.2-5.5 (m, 8H), 6.11 (dt, J 15.0, J 6.5, 1H), 6.37 (dd, J 15.0, J 11.3, 1H), 7.26 (br d, J 11.3, 1H); δc(75 MHz) 12.16, 14.24, 20.53, 25.52, 25.61, 25.67, 26.57, 33.24, 124.44, 126.34, 126.97, 127.82, 128.04, 128.21, 128.54, 128.70, 128.74, 132.01, 140.79, 143.47, 174.28.

Provenance & Evidence