Potassium Iodide → Raloxifene

Participants

Reaction Conditions

Reaction Steps

A 1.5 g. portion of 6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-(4-bromoethoxybenzoyl)-benzo[b]thiophene, hydrochloride, was combined with 25 ml. of dimethylformamide, 5 ml. of piperidine and 150 mg. of potassium iodide, and was stirred for two hours at ambient temperature. The reaction was then heated to 110° C. in an oil bath, under a nitrogen atmosphere, and stirred for 5 days. The course of the reaction was followed by thin layer chromatography on silica gel plates, using a 9/1 mixture of chloroform/methanol as the eluting solvent. As the reaction went on, the spot indicating the protected comopund gradually disappeared, and was replaced, first by spots indicating the two possible mono-protected compounds, and then by a spot indicative of the desired product.

Provenance & Evidence