Dimethyl Sulfoxide → HCID 10380396, compound

A solution of 1.62 ml (22.73 mmol) of dimethylsulfoxide in 60 ml dry methylene chloride is cooled to -78° and 1.44 ml (16.53 mmol) oxalyl chloride is added dropwise. The mixture is stirred for 0.5 h at -78° and a solution of 1.0 g (3.31 mmol) of 1-(3-pyridyl)-4-hydroxy-8-(2-tetrahydropyranyloxy)-octane [=5-hydroxy-8-(3-pyridyl)-1-(2-tetrahydropyranyloxy)-octane, see example 37] in 15 ml dry methylene chloride is added and the mixture is stirred for 10 min at -78°. The mixture is warmed to -60° and maintained for 15 min at that temperature. The reaction is quenched by the addition of 6.9 ml triethylamine. The cold bath is removed and the mixture allowed to warm to room temperature. The reaction mixture is extracted with 150 ml methylene chloride and washed with saturated sodium bicarbonate solution. The organic phase is dried, filtered, concentrated and chromatographed using 3:2 ethyl acetate/hexane to yield 1-(3-pyridyl)-4-oxo-8-(2-tetrahydropyranyloxy)-octane; NMR (CDCl3): delta 2.6 (t,2H), 2.4 (t,4H).