Tin tetrachloride → HCID 69412293, compound

Participants

Reaction Steps

A mixture of yielded (6-benzo[b]thiophen-2-yl-1-chloro-naphthalen-2-yloxy)-acetic acid ethyl ester (2.7 g, 6.8 mmol), valeryl chloride (3.9 mL, 33 mmol) in four portions and tin (IV) chloride (6.4 mL, 56 mmol)in four portions in chloroform (55 mL) was refluxed for five hours. It was then allowed to cool to ambient temperature and poured into ice water. It was diluted with additional chloroform and washed with water and brine. It was then dried with anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was purified three times by flash chromatography (Biotage apparatus) using (1) 25–60% methylene chloride in hexane, (2) 20–40% 1,2-dichloroethane in hexane and (3) 2.5–7.5% methyl t-butyl ether in hexane. It was then purified by HPLC using 92% acetonitrile (0.1% trifluoroacetic acid) in water as the mobile phase. Evaporating the solvent and extracting with ethyl acetate, washing with water and brine, drying with anhydrous magnesium sulfate, filtering, concentrating and drying in vacuo at 60° C. for 20 minutes yielded [1-chloro-6-(3-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester as an olive gum (0.0702 g, 2.14%).

Provenance & Evidence