反应详情

A solution of 5-cyanomethyl-thiophene-3-carboxylic acid (2.7 g, 16.1 mmol) in THF (95 mL) is treated with borane dimethylsulfide (1.78 mL, 10.0 M, 17.8 mmol) in a dropwise maner. After the addition is complete, the solution is warmed to reflux for 1 h. After cooling, water is added and the mixture is extracted with dichloromethane (3×). The combined extracts are dried over Na2SO4, filtered and concentrated in vacuo. The residue is purified by flash chromatography (silica gel, 30-50% ethyl acetate in heptane) to give (4-hydroxymethyl-thiophen-2-yl)-acetonitrile (1.7 g, 69%) as a white solid: mp 45-47° C.; 1H NMR (CDCl3, 300 MHz) δ 7.16 (s, 1 H), 7.02 (s, 1 H), 4.60 (s, 2 H), 3.84 (s, 2 H), 1.79 (s, 1 H).

1. additionAfter the addition
2. temperaturethe solution is warmed
3. temperatureto reflux for 1 h
4. temperatureAfter cooling
5. extractionthe mixture is extracted with dichloromethane (3×)
6. dry with materialThe combined extracts are dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue is purified by flash chromatography (silica gel, 30-50% ethyl acetate in heptane)