HCID 67688225, compound → HCID 67688198, compound

HRID 2257232Notes

Reaction equation

HRID 2257232 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>[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

3

Reactant 1

HCID 67688225HCID 67688225, compound

Product 1

HCID 67688198HCID 67688198, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-3,4-Dihydroxy-5-[(Z)-3-octadecenyl]-2(5H)-furanone was prepared as for the S-isomer from (R)-4-hydroxy-5-[(Z)-3-octadecenyl]-3-[(E)-propenyloxy]-2(5H)-furanone in similar yield: mp 65°-67° C.; [α]D25 9.5° (c=0.5 CH3OH); IR (neat, cm-1) 3421 (br), 2917, 2850, 1754, 1666, 734, 719; 1H NMR (CD3COCD3) δ 5.49-5.28 (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 C22H38O4 (M+), 366.2770 found 366.2780; analysis calculated for C22H38O4 +0.33 H2O: C, 70.93; H, 10.46: Found: C, 70.53; H, 10.25.

Sources & evidence

ORD record
ord-1e00506cbf97412db12ebd455a169773
Source dataset
uspto-grants-1997_08
Patent number
US05656662

Reaction notes

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