1,2-Dibromoethane → (2,3-Dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of 5-benzyloxy-2-(hydroxymethyl)-4(1H)-pyridinone (2 g, 8.7 mmole) and NaOH (680 mg, 17 mmole) in water (220 mL) was hydrogenated over 10% palladium on charcoal (1 g). After 4 hr, the mixture was filtered and the filtrate was concentrated to dryness. The resulting white solid was dissolved in DMF (8 mL) then treated with potassium carbonate (2.9 g, 21 mmole) and 1,2-dibromoethane (0.6 mL, 7 mmole). The mixture was heated at 85° C. overnight. The cooled mixture was concentrated onto silica gel and chromatographed (gradient elution: 10-30% MeOH/EtOAc) to afford the title compound (250 mg, 17%) as a white solid: MS (APCI+) m/e 168 (M+H)+.

Provenance & Evidence