Benzyl Bromide → HCID 12085336, compound

Participants

Reaction Steps

Under argon, 8.9 mmol of a 60% strength suspension of sodium hydride in paraffin oil are added a little at a time to 1.86 g of ethyl 7-hydroxy-6-methoxy-2-chromancarboxylate in 23 ml of dimethylformamide. The mixture is stirred at room temperature for 60 minutes, and 8.1 mmol of benzyl bromide are then added. The reaction mixture is stirred at room temperature for 5 hours. For aqueous work-up (three times washing with water, once with saturated sodium chloride solution), the mixture is diluted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated. Two recrystallizations from cyclohexane give pure ethyl 7-(benzyloxy)-6-methoxy-2-chromancarboxylate; further product fractions are obtained from the mother liquors of the recrystallizations by preparative HPLC purification (column; chromsil, mobile phase: acetonitrile/water).

Provenance & Evidence