Chloromethyl Methyl Ether → 3-(Methoxymethoxy)pyridine

To a mixture of 3-hydroxypyridine (50.0 g, 0.525 mol), tetrahydrofuran (107 mL) and N,N-dimethylformamide (285 mL), potassium t-butoxide (65 g, 0.579 mol) was added at −15° C. After 25 minutes, chloromethyl methyl ether (44.4 g, 0.552 mol) was slowly added at −15° C. The reaction temperature was elevated over 2 hours and the reaction mixture was concentrated. The resulting oil was poured into saturated aqueous sodium chloride and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50) to give 3-(methoxymethoxy)pyridine (54.7 g, 75%).

1. additionwas added at −15° C
2. waitThe reaction temperature was elevated over 2 hours
3. concentrationthe reaction mixture was concentrated
4. additionThe resulting oil was poured into saturated aqueous sodium chloride
5. extractionextracted with ethyl acetate
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50)

ORD record

ord-b6e633e11cb6484f83d05a542b5f9275

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439232B2