Chloromethyl Methyl Ether → HCID 18182399, compound

Participants

Reaction Steps

63 g of potassium carbonate and 300 ml of N,N-dimethylformamide were added to 100 g of 2-benzyl-6-(tert-butyldimethylsilyl)oxymethyl-3-hydroxypyridine and 23 ml of chloromethyl methyl ether was added dropwise into the mixture at room temperature under stirring using a mechanical stirrer. After heating under stirring at 50° C. for 2 hours in an oil bath, water was added thereto and the mixture was extracted with ethyl acetate. Further, the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The resulting residue was dissolved by adding 400 ml of tetrahydrofuran and 300 ml of a tetrahydrofuran solution containing 1 mol of tetra-n-butylammonium fluoride was added thereto under ice-cooling. After stirring under ice-cooling, water was added thereto and the mixture was extracted with ethyl acetate. Further, the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was dissolved in 50% ethyl acetate/hexane and filtered through silica gel. The filtrate was evaporated and dried, to give 73 g of the target compound.

Provenance & Evidence