Potassium tert-butoxide → 3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-ol
Reaction equation
Cl[C:2]1[C:7]([CH:8]([OH:12])[CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=[CH:4][N:3]=1.CC([O-])(C)C.[K+]>CC(O)(C)C>[O:11]1[C:2]2=[N:3][CH:4]=[CH:5][CH:6]=[C:7]2[CH:8]([OH:12])[CH2:9][CH2:10]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 1-(2-chloropyridin-3-yl)propane-1,3-diol (62.9 mmol) and KOtBu (189 mmol) in 240 mL tBuOH (dried over 3 Å molsieves) was heated to 80° C. for 2.5 h. The reaction mixture was then concentrated to about ¼ of its volume, diluted with water and extracted 5 times with DCM. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification with CC (KP-SIL™ from Biotage) using MeOH/DCM (99/1 to 95/5) gives the desired compound as orange oil.
Workup
- concentrationThe reaction mixture was then concentrated to about ¼ of its volume
- additiondiluted with water
- extractionextracted 5 times with DCM
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customPurification with CC (KP-SIL™ from Biotage)
Sources & evidence
- ORD record
- ord-5bd51ae5cc2e4711b27dec943056cdfe
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409917B2
Reaction notes
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