Ethyl bromoacetate → Methyl [1-methyl-2-[3-(3-thienyl)phenoxy]ethoxy]acetate

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Reaction Steps

0.68 g of 1-[3-(3-thienyl)phenoxy]-2-propanol [synthesized by reducing 3-(3-thienyl)phenoxyacetone, prepared by the reaction of 3-(3-thienyl)phenol and monobromoacetone in the presence of potassium carbonate, with sodium borohydride in ethanol] was dissolved in 7 ml of dimethylformamide, and 48 mg of 60% oily sodium hydride was added. After the mixture was stirred at room temperature for 20 minutes, 0.12 ml of ethyl bromoacetate was added. The mixture was stirred at room temperature for 2 hours, and then ethyl ether and water were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane/ethyl acetate=10/1] to give 0.12 g of methyl [1-methyl-2-[3-(3-thienyl)phenoxy]ethoxy]acetate as a colorless oil.

Provenance & Evidence