Chloromethyl Methyl Ether → HCID 21942282, compound

Participants

Reaction Steps

12 g of 2-benzyl-3-hydroxy-6-iodopyridine was dissolved in 50 ml of tetrahydrofuran and 3.8 ml of chloromethyl methyl ether was added thereto. While stirring in an ice bath, 2 g of 60% oily sodium hydride was portionwise added to the mixture. After the addition of sodium hydride, the refrigerant was removed and the mixture was stirred at room temperature for 2.5 hours. Thereafter, in an ice bath, ice water was portionwise added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed and the residue was purified by silica gel column chromatography (15% ethyl acetate/hexane), to give 13 g of the title compound.

Provenance & Evidence