Phosphorus oxychloride → 7-Chloro-2-(trimethylsilyl)furo[3,2-b]pyridine
Reaction equation
[CH3:1][Si:2]([CH3:14])([CH3:13])[C:3]1[O:11][C:10]2[C:5](=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=2)[CH:4]=1.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[CH:4]=[C:3]([Si:2]([CH3:14])([CH3:13])[CH3:1])[O:11][C:10]=12Participants
3
Conditions
- Temperature
- 100 °C
Procedure
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
Workup
- temperatureThe reaction was cooled to RT
- additionpoured into a beaker
- washwashing with minimal DCM
- temperaturecooled in a brine bath
- additionSaturated sodium bicarbonate solution was added very slowly
- additionsolid sodium bicarbonate was added portion wise until the solution
- extractionThe solution was extracted twice with DCM
- dry with materialthe combined organic layers were dried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe material was purified via column chromatography (gradient elution 5-40% EtOAc:Hex)
Sources & evidence
- ORD record
- ord-eabfc079b7824e7f8918f2d8c7d25fe0
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557816B2
Reaction notes
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