3-(4-(Tert-butyldimethylsilyloxy)cyclohex-1-enyl)-2-fluoropyridine → 4-(2-Fluoropyridin-3-YL)cyclohex-3-enol
Reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([C:15]2[C:16]([F:21])=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH2:10]1)(C(C)(C)C)(C)C>ClCCl>[F:21][C:16]1[C:15]([C:12]2[CH2:13][CH2:14][CH:9]([OH:8])[CH2:10][CH:11]=2)=[CH:20][CH:19]=[CH:18][N:17]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a flask containing 3-(4-(tert-butyldimethylsilyloxy)cyclohex-1-enyl)-2-fluoropyridine (1.5 g, 4.88 mmol) was added anhydrous dichloromethane (48.8 mL) under nitrogen. After cooling to 0° C., hydrogen fluoride-pyridine complex (1.696 mL, 19.51 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred until the starting material had been consumed. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with dichloromethane before drying over magnesium sulfate, filtering, and concentrating to a clear oil under reduced pressure. The material was used without purification.
Workup
- additionhydrogen fluoride-pyridine complex (1.696 mL, 19.51 mmol) was added dropwise
- temperatureThe reaction mixture was warmed to room temperature
- customhad been consumed
- customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate
- extractionextracted with dichloromethane
- dry with materialbefore drying over magnesium sulfate
- filtrationfiltering
- concentrationconcentrating to a clear oil under reduced pressure
- customThe material was used without purification
Sources & evidence
- ORD record
- ord-f3968f3515b04f85b81439e1a9dfa38e
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318718B2
Reaction notes
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