HCID 67688157, compound → HCID 67688225, compound

HRID 2257231Notes

Reaction equation

HRID 2257231 reaction equation
[CH2:1]([O:4][C:5]1[C:6](=[O:29])[O:7][C@H:8]([CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:9]=1[OH:10])[CH:2]=[CH2:3]>CO>[OH:10][C:9]1[C@@H:8]([CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[O:7][C:6](=[O:29])[C:5]=1[O:4]/[CH:1]=[CH:2]/[CH3:3]

Participants

3

Reactant 1

HCID 67688157HCID 67688157, compound

Product 1

HCID 67688225HCID 67688225, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-4-Hydroxy-5-[(Z)-3-octadecenyl]-3-[(E)-propenyloxy]-2(5H)-furanone was prepared as for the S-isomer from (R)-3-Allyloxy-4-hydroxy-5-[(Z)-3-octadecenyl]-2(5H)-furanone in similar yield: mp 42°-45° C.; [α]D25 12.8° (c=0.3, CH3OH); IR (neat, cm-1) 3079 (br), 3004, 2919, 1739, 1681, 1658, 738, 721; 1H NMR (CD3COCD3) δ 6.43-6.36 (m, 1H), 5.49-5.31 (m, 2H), 5.05-4.91 (m, 1H), 4.77 (dd., J=3.5, 7.8 Hz, 1H), 2.24-1.62 (m, 6H), 1.51 (dd, J=1.7, 6.9 Hz, 3H), 1.44-1.24 (m, 24H), 0.87 (t, J=6.8 Hz, 3H); HRMS calculated for C25H42O4 (M+) 406.3083, found 406, 3076.

Sources & evidence

ORD record
ord-8387f93f4aef4110a4f35a29be3ee833
Source dataset
uspto-grants-1997_08
Patent number
US05656662

Reaction notes

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