Water → 3-[2-(Methoxyethoxymethoxy)ethyl]-2-methylthiothiophene

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-bromo-3-[2(methoxyethoxymethoxy)ethyl]thiophene (51.8 g, 0.175 mol) in anhydrous ether (125 ml) cooled to -70° C. was added n-butyl lithium (109.4 ml of a 1.6M solution in hexane, 0.175 mol) under a nitrogen atmosphere over a 11/2 hour period. A tan suspension resulted which was stirred for an additional 1 hour and then was diluted with dry THF (100 ml) and was passed under nitrogen into a stirred solution of dimethyldisulfide (18.8 g, 0.20 mol) in anhydrous ether (50 ml) at -15° C. The resulting mixture was stirred at -15° C. for 1/2 hour and at reflux for 2 hours. The dark mixture was cooled to 0° C. and water (100 ml) was added carefully. The organic layer was separated and washed with saturated NaCl solution, dried over anhydrous Na2SO4, filtered and concentrated in vacuo at room temperature. The crude liquid (44.6 g) was distilled, the product being collected at 110-140° C. at 0.7 mm to give 34.6 g of pure product. Yield 75%. NMR supported the structure.

Provenance & Evidence