Hydrochloric Acid → HCID 25010325, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl (2E,7Z,10Z,13Z,16Z,19Z)-3-methyl-docosa-2,7,10,13,16,19-hexaenoate (3) was dissolved in methanol (9 ml) and added LiOH (220 mg, 4.89 mmol) in water (3 ml) and the mixture was heated at 50° C. for 2 hrs. The mixture was cooled, and diluted hydrochloric acid was added to pH 2. Extraction with diethylether, drying (MgSO4) and evaporation of solvents under reduced pressure afforded the acid 4. The acid was purified by flash chromatography on silica gel (8:2 hexane-EtOAc); δH(300 MHz) 0.95 (t, J 7.5, 3H, CH3), 1.55 (m, 2H), 2.0-2.2 (m, 6H), 2.15 (d, J 1.3, 3H, CH3), 2.7-2.9 (m, 8H), 5.2-5.5 (m, 10H), 5.68 (br s, 1H); δc(75 MHz) 14.24, 19.04, 20.53, 25.51, 25.60, 25.62, 25.64, 26.67, 27.28, 40.67, 115.24, 126.99, 127.84, 128.05, 128.11, 128.19, 128.22, 128.53, 128.57, 129.23, 132.00, 163.05, 172.31.

Provenance & Evidence