Ethylene Glycol → 2-(Thiophen-3-yloxy)-ethanol

Participants

Reaction Steps

Using the same reaction conditions as those of Example 7, sodium (2.0 g) in ethylene glycol (125 ml), copper (II) oxide (1.25 g) and potassium iodide (0.05 g) were reacted with 3-bromothiophene (5.0 g, 0.031 mol). Chromatography of the crude product on a silica column eluted initially with dichloromethane, then with a mixture of dichloromethane/methanol (95:5) yielded 3-(hydroxyethoxy)thiophene, as a white solid (1.9 g, 43%). M.p. 38°-39° C. (Found: C, 49.2; H, 5.3; S, 21.9. Calculated for C6H8O2S: C, 50.0; H, 5.6; S, 22.3%); EI m/e Intensity (%): 144 (100, M+), 100 (47, C4H4OS), 45 (17, C2H5O); δH(CDCl3) 6.10-7.11 (3H, m), 4.16 (2H, m), 3.84 (2H, m); δC(CDCl3): 60.8, 71.4, 97.7, 119.4, 124.8, 157.4 ppm.

Provenance & Evidence