Water → HCID 19600806, compound

Participants

Reaction Steps

To a solution of 3-hydroxypyridine (8.56 g, 90.0 mmol) in 300 ml anhydrous DMF was added portionwise 3.6 g of 60% NaH in oil (90 mmol. 1.0 eq.). Stirring 0.5 hour was followed by the addition of 30.0 g (90.0 mmol, 1.0 eq.) of 3-bromo-6-benzyloxy-4-chromanone in one portion. After 1 hour, the reaction was poured into 1 liter H2O and extracted 3×250 ml ethyl acetate. The organic layers were combined, washed 1×100 ml H2O, 1×100 ml 10% LiCl and 1×100 ml brine, then dried over Na2SO4. Filtration and solvent removal afforded 40 g crude product. Silica gel chromatography with 1:4 ethyl acetate:CH2Cl2 as eluant afforded 1.13 g (3.6%) of purified title product; m.p. 133°-134° C.

Provenance & Evidence