Water → (5-(2-Fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methanol
Reaction equation
[Si]([O:18][CH2:19][C:20]1[N:25]=[C:24]([CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:23]([C:31]2[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:32]=2[F:39])=[CH:22][CH:21]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[F:39][C:32]1[CH:33]=[CH:34][C:35]([O:37][CH3:38])=[CH:36][C:31]=1[C:23]1[CH:22]=[CH:21][C:20]([CH2:19][OH:18])=[N:25][C:24]=1[CH2:26][C:27]([CH3:28])([CH3:30])[CH3:29]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-((tert-butyldiphenylsilyloxy)methyl)-3-(2-fluoro-5-methoxyphenyl)-2-neopentylpyridine (10.0 g) in THF (50 mL) was added a 1.0 M solution of tetrabutylammonium fluoride in THF (55.0 ml), and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (3.00 g) as a white amorphous solid.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)
Sources & evidence
- ORD record
- ord-bd11c4f63706424cb1662bc80dade53d
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181186B2
Reaction notes
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