Diethyl Ether → HCID 18980146, compound

Participants

Reaction Steps

A stirred solution of diisopropylamine (3.6 ml, 0.026 mole) in dry THF (60 ml) at -60° C. under argon was treated with 1.5M methyllithium in ether (15.3 ml, 0.023 mole). After 15 minutes, the solution was treated dropwise over 5 minutes with a solution of methyl phenyl sulphone (2.8 g, 0.020 mole) in dry THF (20 ml). The mixture was kept at -60° C. for a further 10 minutes, then treated with a solution of N-methoxy-N-methyl-4-bromo-3-methylbenzamide (D41, 4.4 g, 0.017 mole) in dry THF (30 ml) and allowed to warm to room temp. over 1.5 h. The reaction mixture was treated with 10% Na2CO3 solution (70 ml), then concentrated in vacuo to approx. 100 ml volume and extracted with ethyl acetate (2×100 ml). The combined extract was dried and concentrated in vacuo to afford the title compound as a pale orange solid (6.0 g, 100%).

Provenance & Evidence