HCID 10944542, compound → HCID 57126821, compound

Participants

Reaction Steps

The latter aldehyde was dissolved in Et2O (20 mL). Under anhydrous conditions, the solution of the aldehyde was added dropwise over 15 min to a stirred solution of 3-butenyl magnesium bromide at -78°. The latter solution had been prepared by diluting 71 mL of a 0.64M solution of the Grignard reagent in Et2O with 155 mL of Et2O. After 1 h, the reaction mixture was diluted with Et2O (100 mL). The resulting mixture was washed with a saturated aqueous solution of NH4Cl and then with brine. The organic phase was dried (MgSO4) and evaporated to dryness. The residue was purified by chromatography (SiO2, eluent: hexane-EtOAc, 9:1) to give (2S,3S)-2-benzyloxy-1-phenyl-6-hepten-3-ol (4.82 g), 1H NMR (CDCl3) δ 7.25 (m, 10H), 5.75 (m,1H), 4.95 (m,2H), 4.40 (dd,2H), 3.50 (m, 2H), 2.90 (m,2H), 2.10 (m,3H), 1.60 (m,2H).

Provenance & Evidence