Chloromethyl Methyl Ether → 2,5-Diphenyl-3-(methoxymethoxy)-thiophene

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To a stirred, ice cooled solution of 2,5-diphenyl-3-hydroxythiophene (0.12 g, 0.5 mmol) in dried N,N-dimethylformamide (2 ml) was added sodium hydride (30 mg of a 60% suspension in mineral oil). When the initial vigorous reaction subsides (ca. 4 minutes), the mixture was allowed to stir at ambient temperatures for 20 minutes and then recooled. Chloromethyl methyl ether (0.055 ml, 0.7 mmol) was then added all at once. After stirring cold for ca. 30 minutes, the mixture was allowed to stir at ambient temperatures for ca. 4 hours and then added to a stirred ether/water mixture. The ether layer was washed 3 times with water, dried over sodium sulfate, filtered, concentrated to a residue, and chromatographed on silica gel (methylene chloride/hexane), to yield 0.13 g of (II). M.S.: M+ =296; NMR: consistent. ##STR27##

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