Methanol → HCID 67688147, compound

HRID 2257230Notes

Reaction equation

HRID 2257230 reaction equation
[OH:1][C:2]1[C@H:6]([CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:5][C:4](=[O:25])[C:3]=1[O:26]/C=C/C.CO>C(O)(=O)C>[OH:26][C:3]1[C:4](=[O:25])[O:5][C@@H:6]([CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 887MethanolHCID 67688140HCID 67688140, compound

Product 1

HCID 67688147HCID 67688147, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  1. additionTo a 100 mL round bottom flask was added, under nitrogen
  2. temperatureThe solution was heated
  3. temperatureat reflux (oil bath) for 15 minutes
  4. temperaturecooled
  5. customthe aqueous acetic acid removed in vacuo
  6. customThe residue was purified over silica gel using 12% methanol in chloroform as eluant
  7. customto give 0.17 g (95%) of white waxy solid

Sources & evidence

ORD record
ord-591e93016cc2468dbe26c667fd3b44fe
Source dataset
uspto-grants-1997_08
Patent number
US05656662

Reaction notes

Loading…