Iodoethane → Methyl 2-(5-indanyloxy)-2-[p-(p-chlorophenoxy)phenyl]butyrate

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Reaction Steps

A solution of 0.015mole of lithium N,N-diisopropylamide (prepared as in example 55) in tetrahydrofuran is chilled to -65° C to -75° C. To the solution is added methyl (5-indanyloxy)[p-(p-chlorophenoxy)phenyl]acetate in tetrahydrofuran. To the mixture is added 4 ml of hexamethylphosphoramide and while chilling to -65° C to -75° C, 4.68 g of ethyl iodide is added. After 2 hr., the mixture is allowed to warm to room temperature and stir overnight. The mixture is poured into water and extracted with ether. The ether extracts are washed with 10% hydrochloric acid, water, saturated NaHCo3, saturated NaCl solution and dried (MgSO4). Evaporation of the solvent gives the product as an oil.

Provenance & Evidence