Dimethyl Sulfoxide → [4-(4-Benzyl-morpholin-2-yl)-phenyl]-(2,6-dimethyl-phenyl)-methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (0.46 mL, 5.4 mmol) in CH2Cl2 (20 mL), was added dropwise DMSO (0.94 mL, 13.2 mmol), at −78° C. Subsequently, a solution of [4-(4-benzyl-morpholin-2-yl)-phenyl]-(2,6-dimethyl-phenyl)-methanol (1.6 g, 4.1 mmol) in CH2Cl2 (30 mL) was added, dropwise, at −78° C. After the addition was complete the mixture was stirred for 30 min., at −78° C., and then Et3N (2.9 mL, 20.8 mmol) was added. After complete addition the mixture was allowed to warm to room temperature, overnight. Next, a 2M aqueous NH4OH solution (30 mL) was added, and the mixture extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to afford [4-(4-benzyl-morpholin-2-yl)-phenyl]-(2,6-dimethyl-phenyl)-methanone (1.5 g), which was used as such in the next step.

Provenance & Evidence