N-Methoxy-N-methylacetamide → HCID 67516439, compound

Participants

Reaction Conditions

Reaction Steps

A 2 M solution of lithium diisoproyl amine (35 ml, 70 mmol) in THF (180 mL) cooled to −78° C. was treated with slow addition of 4-bromo-N,N-diethyl-2-methylbenzamide (19 g, 70 mmol) in dry THF (180 mL). The reaction was allowed to stir at −78° C. for 1 hour before it was quenched with N-methoxy-N-methylacetamide (22 mL, 210 mmol) and allowed to slowly warm to room temperature. The reaction was stirred overnight and then partitioned between 1 N HCl (200 mL) and EtOAc (400 mL). The aqueous layer was further extracted with EtOAc (2×150 mL). The combined organic layers were washed with brine (150 mL), dried over magnesium sulfate, filtered and concentrated. The crude material was an orange/brown oil out of which the product crystallizes. The oil was decanted off and the solid was washed with hexanes and dried using a Büchner funnel to afford 4-bromo-N,N-diethyl-2-(2-oxopropyl)benzamide.

Provenance & Evidence