Water → HCID 86702775, compound

Participants

Reaction Conditions

Reaction Steps

p-Methylphenethyltriphenylphosphonium bromide (2.90 g, 6.29 mmol, 1.0 equiv.) in THF (12 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 3.9 mL, 6.29 mmol, 1.0 equiv.) at 0° C., the red solution was stirred at 65° C. for 1 h. The mixture was re-cooled to 0° C., 2-methylundecanal (1.74 g, 9.43 mmol, 1.5 equiv.) in THF (5 mL) was added, and the mixture was stirred at 65° C. for 16 h. After addition of H2O, the aqueous layer was extracted with cyclohexane (2×), the combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3) to yield 1.24 g (69%) of the title compound as a colorless oil.

Provenance & Evidence