Potassium Carbonate → {3-[2-(Tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridin-2-yl}methanol

Participants

Reaction Steps

A suspension of 85% pure 2-(hydroxymethyl)pyridin-3-ol hydrochloride (24.9 g, 130 mmol) and potassium carbonate (60 g, 434 mmol) in acetonitrile (200 mL) was heated at reflux for 15 minutes after which 2-(2-bromoethoxy)tetrahydro-2H-pyran (32.9 g, 160 mmol) was added in one portion and the heating was continued overnight. Solids were filtered off and the solvent was removed under reduced pressure and the resulting oil was chromatographed on a column of silica (100 mm, i.d.=60 mm) with CHCl3 as eluent followed by CHCl3/MeOH/NH4OH (95:5:0.2) to give 28.4 g (93%) of the title compound as a light brown oil. HRMS m/z calcd for C13H19NO4 (M)+ 253.1314. found 253.1326.

Provenance & Evidence