反应详情

To a solution of 1-benzothien-7-yl methyl ether (1 g, 6.1 mmol) in THF (12 mL) at −78° C. was added a solution of 2.5 M n-butyllithium in hexanes (2.9 mL, 7.3 mmol). After stirring for 1.5 hr this solution was added dropwise to a solution of tosyl cyanide (1.66 g, 9.1 mmol) in THF (8 mL), this was left stirring at −78° C. for 0.5 hr and then warmed to room temperature. After 16 h this was poured onto ice-water and extracted with dichloromethane (3×50 mL). The combined organic extracts were washed with water, dried (MgSO4) and the solvent removed in vacuo to give an oil. This was purified by flash chromatography with a gradient of 0–30% ethyl acetate in hexane to give the title compound (0.31 g, 27%); δH (300 MHz, CDCl3) 7.79 (1H, s, 3-ArH), 7.46–7.38 (1H, m, 4-ArH), 7.37–7.31 (1H, m, 5-ArH), 6.88–6.82 (1H, m, 6-ArH) and 3.94 (3H, s, OCH3). Starting material 1-benzothien-7-yl methyl ether was recovered from the reaction (0.56 g, 56%); δH (300 MHz, CDCl3) 7.45–7.29 (4H, m, ArH), 6.75 (1H, m, ArH), 4.00 (3H, s, OCH3).

1. waitthis was left
2. stirringstirring at −78° C. for 0.5 hr
3. additionAfter 16 h this was poured onto ice-water
4. extractionextracted with dichloromethane (3×50 mL)
5. washThe combined organic extracts were washed with water
6. dry with materialdried (MgSO4)
7. customthe solvent removed in vacuo
8. customto give an oil
9. customThis was purified by flash chromatography with a gradient of 0–30% ethyl acetate in hexane