Dimethyl Sulfoxide → HCID 86662315, compound

Participants

Reaction Conditions

Reaction Steps

An oven dried flask (50 ml, round bottom) containing dry dichloromethane (13 ml) is cooled to −78° C. (dry ice/acetone bath) under argon atmosphere. Oxalyl chloride (0.23 ml, 2.67 mmol) is added followed by the addition of dry dimethyl sulfoxide (0.31 ml, 4.31 mmol) via drop-wise addition. The mixture is stirred for 10 minutes and then a solution of 2-(6-chloropyridin-3-yloxy)-2-methylpropan-1-ol (451 mg, 2.06 mmol) [dissolved in dichloromethane (4 ml)] is added via slow drop-wise addition. The cooled solution was stirred for 30 minutes and then triethylamine (1.15 ml, 8.2 mmol) was added and the cooling bath was removed. The mixture was stirred and warmed to ambient over 1 hour. A saturated solution of sodium bicarbonate (20 ml) was added and also dichloromethane (20 ml). The material was transferred and shaken in a reparatory funnel. The dichloromethane phase was collected and washed with brine solution (25 mL). The aqueous phase was back extracted with methylene chloride (2×20 mL) and the organic phases combined, dried over magnesium sulfate, filtered and stripped. The material was purified by filtration through a short column of silica gel (20 g), eluting with 30% ethyl acetate/hexanes, which provided the product as a light yellow oil (361 mg). (M+H)+=200 m/e.

Provenance & Evidence