Chloromethyl Methyl Ether → 2-chloro-5-(MethoxyMethoxy)pyridine
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[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].[CH3:11][O:12][CH2:13]Cl>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][O:12][CH3:13])=[CH:4][N:3]=1[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].[CH3:11][O:12][CH2:13]Cl>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][O:12][CH3:13])=[CH:4][N:3]=12-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).
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