Thionyl Chloride → 4-chloro-3,4-dihydro-2H-pyrano[2,3-b]pyridine
Reaction equation
[O:1]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[CH:4](O)[CH2:3][CH2:2]1.S(Cl)([Cl:14])=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:14][CH:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[O:1][CH2:2][CH2:3]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of 3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-ol (21 mmol) in 80 mL DCM was added 2.3 mL thionyl chloride at 0° C. The reaction mixture was stirred at 0° C. for 10 min and then at reflux for 30 min. After cooling to RT, sat. aq. NaHCO3 solution was added and the mixture was extracted 3 times with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo to obtain the desired product as orange oil.
Workup
- temperatureat reflux for 30 min
- temperatureAfter cooling to RT
- extractionthe mixture was extracted 3 times with EtOAc
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-9267b759841140508738ad2b29e70490
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409917B2
Reaction notes
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