Sodium Hydroxide → (2,3-Dihydro-[1,4]dioxino[2,3-B]pyridin-6-YL)methanol

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Reaction Steps

To a stirred solution of (2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)methyl acetate (75.0 g, 0.36 mol) in MeOH (500 mL) was added aqueous NaOH (2M, 350 mL, 0.72 mol) dropwise at 0° C. After the addition, the mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was diluted with water (250 mL). The aqueous solution was washed with CH2Cl2 (2×200 mL). The combined organic layers were washed with brine (2×100 mL), dried over anhydrous Na2SO4 and concentrated to yield (2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)methanol (48.0 g, 80%) as a grey solid. The crude material was used directly in the next step.

Provenance & Evidence