Tetraethylene Glycol → Thiophene

Participants

Reaction Steps

Butoxyethoxyethoxyethoxyethanol (25.0 g, 0.1 mol) was prepared from tetraethylene glycol, sodium hydroxide and butyl chloride (10:1:1) by a method known in the art and then reacted with potassium metal (3.9 g, 0.1 mol) at room temperature for 1.5 hours in tetrahydrofuran. 3-(Bromomethyl)thiophene (17.7 g, 0.1 mol) was added dropwise, and the mixture stirred under reflux for 24 hours. After cooling and filtration the tetrahydrofuran was removed in vacuo and the residue dissolved in methylene chloride, washed with water and dried with potassium carbonate. The solvent was removed and the crude oil distilled to give 3-butoxyethoxyethoxyethoxyethoxymethyl)thiophene (25.7 g, 57%). B.p. 162°-163° C./0.15 mm Hg. (Found: C, 58.6; H, 8.7; S, 9.5. Calculated for C17H30O5S: C, 58.9; H, 8.7; S, 9.3%); EI m/e Intensity (%): 346 (9, M+), 97 (100, C4H3S.CH2), 57 (75, C4H9); δH(CDCl3): 7.26 (1H, m) 7.20 (1H, m), 7.06 (1H, m), 4.56 (2H, s) 3.65 (16H, m), 3.45 (2H, t), 1.53 (2H, m), 1.34 (2H, m) and 0.91 (3H, t); δC(CDCl3): 13.6, 18.9, 31.4, 68.1, 69.0, 69.8, 70.0, 70.3, 122.5, 125.5, 126.7, 139.1 ppm.

Provenance & Evidence