Dimethylformamide → HCID 22223280, compound

Participants

Reaction Steps

To a cold (−78° C.) solution of hydroquinone 3 (17.00 g, 96.6 mmol) in DMF under N2 was added unwashed 60% sodium hydride in mineral oil (8.90 g, 222.5 mmol). The resultant reaction mixture was warmed to room temperature over a 30 min period and subsequently treated with methyl iodide (14.3 mL, 230 mmol). After stirring the reaction mixture for 1 hr at room temperature the reaction mixture was diluted with ethyl acetate (1.5 L) and washed with brine (3×500 ml). The organic solution was dried over sodium sulfate, filtered, concentrated, and the residue purified on silica gel (elution with 20% ethyl acetatehexane) to afford 4 as a light yellow oil which solidified upon standing.

Provenance & Evidence