HCID 67688208, compound → HCID 67688140, compound

Participants

Reaction Steps

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.

Provenance & Evidence