Dimethyl Sulfoxide → 2,6-Diisopropyl-4-(4-fluorophenyl)-pyridine-3,5-dicarbaldehyde

Participants

Reaction Conditions

Reaction Steps

To solution of 16 ml (0.18 mol) oxalyl chloride in 150 ml dry diohloromethans was added, et -78° C., 40 ml dimethyl sulfoxide over a period of 5 minutes. After 10 minutes, 26 g (0,082 mol) of the product of step 3 in 200 ml of 1:3 solution dimethyl sulfoxide/dichloromethane was added dropwise. This reaction mixture was stirred at -78° C. for 20 minutes, before it was quenched with 80 ml triethylamime. The cooling bath was removed and the reaction was allowed to warm to room temperature. The reaction was partitioned between ethyl acetate (500 ml) and 1N hydrochloric acid (200 ml). The organic layer was washed With water (4×100 ml) and brine and dried over magnesium sulfate and filtered. Evaporation of the filtrate in vaouo gave 24.5 g of the Step 4 title product as a viscous oil which was used without further purification.

Provenance & Evidence