Chloromethyl Methyl Ether → 3-(Methoxymethoxy)pyridine

Participants

Reaction Conditions

Reaction Steps

Dissolve 3-hydroxypyridine (7 g, 74 mmol) in THF (20.6 mL) and DMF (34.4 mL) and cool to −15° C. Add potassium tert-butoxide (8.3 g, 74 mmol) and stir at −15° C. for 30 min. Treat the mixture with chloromethylmethyl ether (5.81 mL, 77 mmol) dropwise over 40 min. After the addition is complete, stir the mixture at −15° C. for an additional 1 h. Remove the ice bath and allow the mixture to warm slowly to 15° C. Pour the mixture into saturated aqueous sodium chloride and stir vigorously for 10 min. Extract the resulting solution with three portions of ethyl acetate. Combine the organic extracts and wash with saturated aqueous sodium chloride, dry over sodium sulfate, filter, and concentrate in vacuo. 1H NMR (400 MHz, CDCl3) δ 8.42 (d, J=3 Hz, 1H), 828 (d, J=5 Hz, 1H), 7.37-7.42 (m, 1H), 7.21-7.27 (m, 1H), 5.20 (s, 2H), 3.49 (s, 3H).

Provenance & Evidence