Water → HCID 53877864, compound

Participants

Reaction Steps

4.71 g of 5-fluoro-2-hydroxybenzyl alcohol [prepared as described in step (a) above] were dissolved in 100 ml of N,N-dimethylacetamide, and then 3.72 g of potassium t-butoxide were added to the resulting solution, whilst ice-cooling. The resulting mixture was then stirred at the same temperature for 10 minutes, and then 2.74 ml of methoxymethyl chloride were added at the same temperature. The mixture was then allowed to stand until the temperature returned to room temperature, after which it was stirred for 1 hour. 60 ml of water and 300 ml of ethyl acetate were then added to the reaction solution. The ethyl acetate layer was separated, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The concentrated substance was purified by silica gel column chromatography, using a 3:2 by volume mixture of hexane and ethyl acetate as the eluent, to give 4.25 g (yield 69%) of the title compound as an oily substance.

Provenance & Evidence