Chloromethyl Methyl Ether → 2-chloro-5-(MethoxyMethoxy)pyridine

2-Chloro-5-hydroxy-pyridine (3 g, 30.9 mmol) in DMF (5 mL) was added to a cold (0° C.) solution of NaH (1.5 g, 37.1 mmol) in DMF (20 mL). The mixture was stirred at 0° C. for 1 h. Chloromethyl methyl ether (4.95 g, 60.8 mmol) was added. The reaction mixture was allowed to warm to rt, stirred overnight, cooled to 0° C., quenched by addition of water, and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate, 98:2) to afford 3 g of the title compound. tR: 0.56 min (LC-MS 2); ESI-MS: 174.0 [M+H]+ (LC-MS 2); Rf=0.67 (hexane/ethyl acetate, 1:1).

1. temperatureto warm to rt
2. stirringstirred overnight
3. temperaturecooled to 0° C.
4. customquenched by addition of water
5. extractionextracted with EtOAc
6. dry with materialThe organic layer was dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate, 98:2)

ORD-Eintrag

ord-e963b5ee7ea24f1d8284273c90b66ffc

Quelldatensatz

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08969341B2