Thionyl Chloride → 4-chloro-3,4-dihydro-2H-pyrano[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence