Water → HCID 21928841, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2.55 g of cyclopropyl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone in 40 cm3 of dimethylformamide is added dropwise at a temperature in the region of 5° C. to a suspension, cooled to this same temperature, of 0.39 g of sodium hydride (at 60% in oil) in 20 cm3 of dimethylformamide. After stirring the mixture at this same temperature for about one and a half hours, a solution of 1.87 g of (2-chloromethoxyethyl)trimethylsilane in 20 cm3 of dimethylformamide is added dropwise without exceeding a temperature of 10° C. After warming to a temperature in the region of 20° C., the mixture is stirred for 2 hours at this same temperature. 20 cm3 of water are then added and the mixture is concentrated under reduced pressure (13 kPa). The residue is taken up in 80 cm3 of water and extracted three times with 60 cm3 of dichloromethane. The combined organic phases are dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure. After flash chromatography on a column of silica [eluent: dichloromethane/methanol (99/1 by volume)], 2.5 g of cyclopropyl(6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazol-3-yl)methanone are thus obtained in the form of a solid, the characteristics of which are as follows:

Provenance & Evidence