Iodoethane → 3-(4-Benzyloxyphenyl)-2-ethoxypropanoic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (55% suspension in oil, 1.65 g) was added to a solution ethyl 3-(4-benzyloxyphenyl)lactate (10.30 g), which is the product of Reference example 1(b), in a mixture of N,N-dimethylacetamide (50 ml) and toluene (50 ml). The mixture was stirred at 40° C. for 30 minutes. To the reaction mixture were added ethyl iodide (3.3 ml) and toluene (5 ml). This mixture was stirred at 40° C. for 2 hours. At the end of this time the reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified via chromatography on a silica gel column using hexane/ethyl acetate=5/1 as the eluant to give the desired compound (5.50 g) as a syrup.

Provenance & Evidence