Dimethylformamide → Dibenzyl ether

Participants

Reaction Steps

Sodium hydride (60%, 79.2 mg) and anhydrous DMF (1 ml) were added to a reactor. A solution of (4aR, 12aR)-4a-(3-hydroxyphenyl)-2-methyl-1,2,3,4,4a,5,12,12a-octahydro-quinolino[2, 3-g]isoquinoline (530 mg, 1.58 mmol) in anhydrous DMF (23 ml), and benzyl bromide (0.20 ml, 1.66 mmol) were added to the reactor, followed by stirring at room temperature for 1 hour. After reaction was completed, an aqueous saturated sodium bicarbonate solution (50 ml), distilled water (50 ml), and toluene (250 ml) were added to the reaction solution, followed by fractionation. The aqueous layer was extracted twice with toluene (150 ml), and the organic layers were together dried over sodium sulfate, filtered, and then concentrated to obtain 531 mg of benzyl ether compound. The thus-obtained compound was supplied to next reaction without purification.

Provenance & Evidence