Water → HCID 67102642, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of triphenylethylvalerate phosphonium bromide (Step A, 13.29 g, 28.2 mmol) and sodium hydride (0.745 g, 31.0 mmol) in dimethyl sulfoxide (40 ml) was stirred for 30 minutes under nitrogen. The reaction mixture was heated to 26.7° C. and 3-(2,6-Dimethylbenzyloxy)benzaldehyde (5.00 g, 20.8 mmol) diluted in dimethyl sulfoxide (20 ml) was added dropwise over 4 minutes. The reaction mixture was stirred for 3 hours at 50° C. A mixture of triphenylethylvalerate phosphonium bromide (Step A, 5.56 g, 118 mmol) and sodium hydride (0.312 g) in dimethyl sulfoxide (15 ml) was stirred under nitrogen for 30 minutes. This mixture was added, in bolus to the above reaction mixture at room temperature. The reaction mixture was stirred for 6 hours at 50° C., cooled to room temperature and poured over ice (60 g) and water (60 ml) mixture. The aqueous mixture was extracted with ethyl acetate (3×150 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated to afford the 14.3 g of brown oil. The oil was dissolved in 30 ml of hexane:ethyl acetate (95:5) and chromatographed on a Biotage 75S silica gel column to give 5.8 g of a yellow oil. The yellow oil was subjected to another silica gel column chromatography eluting with hexane:chloroform (1:1) to hexane:ethyl acetate (9:1) to afford 3.74 g (51%) of a dark yellow oil.

Provenance & Evidence