Tetrabutylammonium Fluoride → Methyl 2,2-dimethyl-4-[3-(3-pyridyl)propyl]8-hydroxyoctanoate
Reaction equation
[CH3:1][C:2]([CH3:30])([CH2:7][CH:8]([CH2:21][CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH2:9][CH2:10][CH2:11][CH2:12][O:13][Si](C(C)(C)C)(C)C)[C:3]([O:5][CH3:6])=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][C:2]([CH3:30])([CH2:7][CH:8]([CH2:21][CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[C:3]([O:5][CH3:6])=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1.85 g (4.2 mmol) of methyl 2,2-dimethyl-4-[3-(3-pyridyl)propyl]-8-(t-butyldimethylsilyloxy)-octanoate in 2 ml dry tetrahydrofuran is added 4.8 ml (4.8 mmol) of 1M tetra-n-butylammonium fluoride in tetrahydrofuran and the mixture is stirred for 1 h. The reaction is quenched by addition of saturated ammonium chloride solution and the mixture is extracted with ethyl acetate. The organic phase is washed with water and brine, dried, filtered and concentrated. The residue is purified by silica gel chromatography using 4:1 ethylacetate/hexane as eluent to yield methyl 2,2-dimethyl-4-[3-(3-pyridyl)propyl]-8-hydroxyoctanoate as an oil; NMR (CDCl3): delta 3.59 (s,3H), 3.6 (m,2H), 2.58 (t,2H), 1.21 (s,6H).
Workup
- customThe reaction is quenched by addition of saturated ammonium chloride solution
- extractionthe mixture is extracted with ethyl acetate
- washThe organic phase is washed with water and brine
- customdried
- filtrationfiltered
- concentrationconcentrated
- customThe residue is purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-4dd879fa756d43d292e294990ae5d256
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05153214
Reaction notes
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