HCID 67688208, compound → HCID 67688140, compound

HRID 2257229Notes

Reaction equation

HRID 2257229 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 67688208HCID 67688208, compound

Product 1

HCID 67688140HCID 67688140, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flame-dried, three-necked 250 mL round bottom flask under argon was added 0.172 g (0.20 mmol) of [bis(methyldiphenylphosphine)](1,5-cyclooctadiene)iridium(1) hexafluorophosphate suspended in 35 mL of freshly distilled peroxide free anhydrous tetrahydrofuran. The flask as evacuated and the argon displaced with hydrogen. The red suspension turned to a colorless solution after 5 minutes. The flask was evacuated, and the hydrogen replaced with argon. (S)-3-allyloxy-4 -hydroxy-5-[(Z)-3-octadecenyl]-2(5H)-furanone (0.415 g, 1.02 mmol) was dissolved in 25 mL of peroxide free tetrahydrofuran and added to the activated catalyst. On completion (TLC; approximately 3 hours) the solvent was evaporated in vacuo and purified over silica gel using 10% methanol in chloroform as eluant to provide 0.33g (79%) of white waxy solid: mp 42°-45° C.; [α]D25 -13.0°(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 406.3083.

Workup

  1. customThe flask as evacuated
  2. customThe flask was evacuated
  3. additionadded to the activated catalyst
  4. customOn completion (TLC; approximately 3 hours) the solvent was evaporated in vacuo
  5. custompurified over silica gel using 10% methanol in chloroform as eluant
  6. customto provide 0.33g (79%) of white waxy solid

Sources & evidence

ORD record
ord-991f9dfa4d09496f9bb906c9da0f51c8
Source dataset
uspto-grants-1997_08
Patent number
US05656662

Reaction notes

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