反应详情

温度

100 °C

2-(Trimethylsilyl)furo[3,2-b]pyridine N-oxide (10.51 g, 50.7 mmol) dissolved in POCl3 (47.3 ml, 507 mmol) in a sealed flask and heated at 100° C. for one hour. The reaction was cooled to RT, poured into a beaker washing with minimal DCM, and cooled in a brine bath. Saturated sodium bicarbonate solution was added very slowly and then solid sodium bicarbonate was added portion wise until the solution was at about pH=8. The solution was extracted twice with DCM, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (gradient elution 5-40% EtOAc:Hex) to afford 7-chloro-2-(trimethylsilyl)furo[3,2-b]pyridine as a pale yellow oil. MS: M+H+=226.2

1. temperatureThe reaction was cooled to RT
2. additionpoured into a beaker
3. washwashing with minimal DCM
4. temperaturecooled in a brine bath
5. additionSaturated sodium bicarbonate solution was added very slowly
6. additionsolid sodium bicarbonate was added portion wise until the solution
7. extractionThe solution was extracted twice with DCM
8. dry with materialthe combined organic layers were dried with sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe material was purified via column chromatography (gradient elution 5-40% EtOAc:Hex)