1,5-Diphenylpentan-3-one → HCID 21635958, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1.59 g (4.45 mmol) of methyltriphenylphosphonium bromide in 100 ml of tetrahydrofuran was cooled to -78° C., treated with 2.2 ml (4.5 mmol) of n-butyllithium, warmed to 0° C, was recooled to -78° C. The resulting solution was treated via cannula with a solution of 1.59 g (4.45 mmol) of 1,5diphenyl-3-pentanone in 20 ml of tetrahydrofuran. After being allowed to stir at ambient temperature for 2 h, the solution was diluted with hexane, washed sequentially with water and saturated brine, dried over MgSO4, and concentrated in vacuo. The mixture was purified by flash chromatography to give 0.90 g (86%) of the desired compound as a colorless oil. 1H NMR (CDCl3) δ 2.37 (t, J=8 Hz, 4H), 2.76 (t, J=8 Hz, 4H), 4.81 (s, 2H), 7.15-7.3 (m, 10H). Mass spectrum (M+NH4)+ =254.

Provenance & Evidence