反应详情

(Ref: Gallagher, T; Pardoe, D. A.; Porter, R. A.; Tetrahedron Lett.; 2000, 41(28), 5415-5418.) To a solution of S-(2-formyl-5-methoxyphenyl) dimethylthiocarbamate (1.08 g, 4.5 mmol) in water (4 mL) and methanol (8 mL) was added sodium hydroxide (199 mg, 4.9 mmol), this was heated to reflux for 16 hours. The reaction was cooled to room temperature and chloroacetonitrile (0.28 mL, 4.5 mmol) was added in one portion and the mixture the stirred at room temperature for 1 hour. The methanol was removed in vacuo, and water (10 mL) added. The aqueous layer was extracted with diethyl ether (3×20 mL), dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography with a gradient of 0-30% ethyl acetate in iso-hexane to give the title compound as a colourless solid (390 mg, 46%); δH (300 M , CDCl3) 7.80-7.70 (1H, m, ArH), 7.29 (2H, m, ArH), 7.11-7.01 (1H, m, ArH) and 3.85 (3H, s, OCH3). M+23=212.0. νmax/cm−1[film] 2213.50 (m).

1. temperaturethis was heated
2. temperatureto reflux for 16 hours
3. customThe methanol was removed in vacuo, and water (10 mL)
4. additionadded
5. extractionThe aqueous layer was extracted with diethyl ether (3×20 mL)
6. dry with materialdried (MgSO4)
7. customthe solvent removed in vacuo
8. customThe residue was purified by flash chromatography with a gradient of 0-30% ethyl acetate in iso-hexane