反应详情

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of S,S-dimethylmethanesulfinyl iodide (1.15 g, 5.23 mmol, 1.60 equiv), t-BuOK (4 mL, 1.20 equiv) in dichloromethane (5 mL) at room temperature After 30 minutes a solution of ethyl 9-bromo-4-oxo-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate (1.2 g, 3.26 mmol, 1.00 equiv) in dichloromethane (10 mL) was added slowly. The resulting solution was stirred for 5 h at room temperature, quenched with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:19) to give 600 mg (48%) of the titled compound as a off-white solid; LC-MS 382,384[M+H]+.

1. customInto a 100-mL 3-necked round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. customat room temperature
4. customAfter 30 minutes
5. additionwas added slowly
6. customquenched with water
7. extractionextracted with dichloromethane
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under vacuum
10. customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:19)