Water → HCID 14685353, compound

Participants

Reaction Steps

Reaction of 3-bromomethylthiophene with sodium methoxide in methanol provided 3-methoxymethylthiophene (84%). n-Butyl lithium (30 ml, 1.5 M, 45 mmol) was slowly added to 3-methoxymethylthiophene (5.0 g, 39 mmol) in dry ether (100 ml) at 25° C. After stirring for 1 h, N,N-dimethylformamide (5.7 g, 78 mmol) in dry ether (200 ml) was added dropwise and the resultant solution was stirred for an additional 18 h at 20° C. Water (5 ml) was added and the organic phase washed with 5% hydrochloric acid (100 ml) followed by water (100 ml) and dried. The solvent was removed to yield the crude product (5.2 g, 85%) which was essentially pure by n.m.r. Distillation afforded the title compound (3.80 g, 62%) as a colourless oil, b.p. 73°-75° C. at 0.25 mmHg (Found M+ : 156.0256. C7H8O2S requires M, 156.0245) which showed νmax (film) 667m, 1107m, 1200w, 1426m, 1662s, 2930w and 3100w cm-1 ; δH (CCl4) 3.35 (3H, s), 4.66 (2H, s), 7.05 (1H, d, J 5 Hz), 7.49 (1H, d, J 5 Hz), 9.87 (1H, s); m/z 156 (M+), 141 (M+ -CH3).

Provenance & Evidence