Hydrochloric Acid → HCID 21862807, compound

Participants

Reaction Steps

0.29 g (7.1 mmol) of sodium hydride (as a 60% w/w dispersion in mineral oil) was added to 50 ml of anhydrous tetrahydrofuran, whilst ice-cooling, and then the mixture was stirred for 10 minutes. At the end of this time, a solution of 2.00 g (6.5 mmol) of diethyl α-(4-methoxyphenacyl)malonate [prepared as described in step (i) above] in 20 ml of anhydrous tetrahydrofuran was slowly added dropwise to the mixture, whilst ice-cooling. The mixture was then stirred for 30 minutes. A solution of 1.72 g (7.1 mmol) of 3-cyclopentyloxy-4-methoxybenzyl chloride in 20 ml of anhydrous tetrahydrofuran and 0.97 g (6.5 mmol) of sodium iodide were then added to the mixture, and the resulting mixture was heated under reflux for 2 hours. At the end of this time, the mixture was cooled to room temperature and was then acidified by the addition of 3N aqueous hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue thus obtained was applied to a silica gel chromatography column and eluted with a 1:4 by volume mixture of ethyl acetate and hexane, to give 2.45 g of the title compound as a pale yellow oily substance.

Provenance & Evidence