Methanol → HCID 67688147, compound

Participants

Reaction Steps

To a 100 mL round bottom flask was added, under nitrogen, 0.2 g (0.49 mmol) (S)-4-hydroxy-5-[(Z)-3-octadecenyl]-3-[(E)-propenyloxy]-2(5H)-furanone was dissolved in 60 mL of 50% aqueous acetic acid. The solution was heated at reflux (oil bath) for 15 minutes, cooled, and the aqueous acetic acid removed in vacuo. The residue was purified over silica gel using 12% methanol in chloroform as eluant to give 0.17 g (95%) of white waxy solid: mp 64°-66°C; [α]D25 -9.9° (C=0.5, CH3OH); IR (neat, cm-1) 3421(br), 2917, 2850, 1754, 1668, 719; 1H NMR (D3COCD3) δ5.49-5.28 (m, 2H), 4.67 (dd, J=3.4, 7.8 Hz, 1H), 2.32-1.88 (m, 4H), 1.69-1.51 (m, 2H), 1.44-1.25 (m,. 24H), 0.87 (t, J=6.7 Hz, 3H); HRMS calculated for C25H38O4 (M+) 366.2770, found 366.2780; analysis calculated for C22H38O4 +0.33 H2O: C, 70.93; H, 10.46; Found: C, 70.73; H, 10.31.

Provenance & Evidence