Octanal → (Z)-6-Tetradecen-1-ol

Participants

Reaction Steps

(6-Hydroxyhexyl)triphenylphosphonium bromide 6 (0.5 g, 1.13 mmol) in warm DMSO (3 ml) was added to THF solution of methylsulfinylmethanide ion (prepared from NaH (57 mg, 2.37 mmol) and DMSO (1 ml) under N2 at 70-75° C. for 80 min) with cooling in an ice-bath. The bright yellow solution of phosphorane was stirred at room temperature for 10 min, then treated with octanal (0.159 g, 1.25 mmol) at 0° C. After stirring for 20 min, the reaction mixture was poured into 5 ml H2O and extracted several times with ether. Drying with MgSO4 and concentration affords a residue which was purified by FCC (14% EtOAc in hexanes) to yield 7 (0.13 g, 54%, lit. 60%); δH(270 MHz, CDCl3) 0.86 (3H, t, J=6.5 Hz), 1.10-1.43 (16H, m), 1.55 (2H, m), 2.00 (4H, m), 3.6 (2H, t, J=6.5 Hz) and 5.3-5.4 (2H, m).

Provenance & Evidence