Chloromethyl Methyl Ether → HCID 67058066, compound

Participants

Reaction Conditions

Reaction Steps

1-{6-[(2′,6′-Dimethylbiphenyl-3-yl)methoxy]pyridin-3-yl}-3-(trityloxy)propan-1-ol (250 mg, 0.413 mmol) produced in Example 31 (31C) was dissolved in dimethylformamide (2.5 mL), and sodium hydride (about 63%, oily, 32 mg, 0.83 mmol) was added thereto at 0° C., and then, the resulting mixture was stirred under a nitrogen atmosphere at 0° C. for 50 minutes. Thereafter, chloromethyl methyl ether (0.063 mL, 0.825 mmol) and tetra-n-butyl ammonium iodide (8.0 mg, 0.021 mmol) were sequentially added thereto at 0° C., and the resulting mixture was stirred under a nitrogen atmosphere at 50° C. for 5 hours. To the reaction solution, a saturated aqueous solution of ammonium chloride was added at 0° C., and the organic matter was extracted with ethyl acetate. The organic layer was washed with water, a saturated sodium bicarbonate solution, and a saturated sodium chloride solution, then dried over anhydrous sodium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 75:25 (v/v)), whereby the objective title compound was obtained (85 mg, yield: 32%).

Provenance & Evidence