反应详情

A mixture of Example 38C (3.68 g, 23.6 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (4.93 g, 23.6 mmol), and K2CO3 (3.26 g, 23.6 mmol) in MeOH (110 mL) was heated to reflux. After 1 hr the reaction mixture was cooled to ambient temperature and the volatiles evaporated at reduced pressure. The residue was partitioned between Et2O and H2O. The separated aqueous phase was extracted with Et2O, and the combined organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Flash chromatography (Analogix® Intelliflash 280™; 5% to 25% EtOAc/hexanes eluant; SF40-150 g column) afforded 4.39 g (89%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.40 (s, 1H), 7.80-7.73 (m, 2H), 7.69 (d, J=8.6, 2H), 7.09 (t, J=55.3, 1H), 2.40 (s, 3H). MS (DCI+) m/z 210 (M+H).

1. customthe volatiles evaporated at reduced pressure
2. customThe residue was partitioned between Et2O and H2O
3. extractionThe separated aqueous phase was extracted with Et2O
4. extractionthe combined organic extract
5. washwas washed with brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo