Water → HCID 19600806, compound

Participants

Reaction Steps

To a solution of 3-hydroxypyridine (8.56 g, 0.090 mol) in 300 ml of dimethylformamide was added NaH (60% in oil, 3.6 g, 0.090 mol). After stirring 0.5 hour, 6-benzyloxy-3-bromo-4-chromanone (30.0 g., 0.090 mol) was added in one portion. After stirring for 1 hour, the reaction mixture was poured into 1 liter of water and extracted 3×250 ml of ethyl acetate. The organic layers were combined, washed 1×100 ml H2O, 1×100 ml 10% LiCl and 1×100 ml brine, dried (Na2SO4) and stripped to yield 40 g of crude title product, which was chromatographed on silica gel using 1:4 ethyl acetate:CH2Cl2 as eluant to yield 1.13 g of purified title product as an off-white powder; mp 133°-134° C. A portion (290 mg) was recrystallized from isopropyl ether to yield 240 mg of white powder.

Provenance & Evidence