Chloromethyl Methyl Ether → HCID 18470782, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-acetyl-4-methyl-2,5-di(4-pyridyl)-1H-pyrrole (1.0 g, 3.6 mmol) in DMF (5 mL) was added NaH (60% oil dispersion; 0.29 g, 7.2 mmol) at room temperature. The mixture was heated at 70-80° C. for 30 minutes, and after cooling to 0° C., chloromethyl methyl ether (0.41 mL, 5.4 mmol) was added. The mixture was stirred for 15 hours, and saturated aqueous NaHCO3 (30 mL) was added to the reaction mixture. The whole was extracted with ethyl acetate (50 mL×3). Combined organic layers were washed with water (50 mL), brine (50 mL), dried over MgSO4, and concentrated in vactio. The residual oil was purified by preparative TLC (1 mm×3) to give the title compound (0.1 g, 9% yield) as a light brown powder.

Provenance & Evidence