Tetrabutylammonium Fluoride → 5-[(4-Chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-1-nonanol
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([C:46]1[CH:51]=[C:50]([F:52])[CH:49]=[CH:48][C:47]=1[F:53])([S:36]([C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1)(=[O:38])=[O:37])[CH2:32][CH2:33][CH2:34][CH3:35])(C(C)(C)C)(C)C>O1CCCC1.C(OCC)C.C(OCC)(=O)C.CCCCCC>[Cl:45][C:42]1[CH:41]=[CH:40][C:39]([S:36]([C:31]([C:46]2[CH:51]=[C:50]([F:52])[CH:49]=[CH:48][C:47]=2[F:53])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:30][CH2:29][CH2:28][CH2:27][OH:26])(=[O:38])=[O:37])=[CH:44][CH:43]=1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
After addition of tetrabutylammonium fluoride (a 1M tetrahydrofuran solution, 0.532 ml, 0.532 mmol) to a solution of 2-[5-(t-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-1-butylpentyl]-1,4-difluorobenzene (154 mg, 0.283 mmol) in tetrahydrofuran (4 ml), the mixture was stirred at room temperature for 18 hours. The reaction mixture was then concentrated. The residue thus obtained was dissolved in diethyl ether, followed by successive washing with water and brine, drying over MgSO4, and concentration. The residue thus obtained was purified by medium-pressure chromatography on a silica gel column (50% ethyl acetate-hexane), whereby the title compound (122 mg, 0.283 mmol) was obtained as a colorless oil.
Workup
- concentrationThe reaction mixture was then concentrated
- customThe residue thus obtained
- washby successive washing with water and brine
- dry with materialdrying over MgSO4, and concentration
- customThe residue thus obtained
Sources & evidence
- ORD record
- ord-8376ad7e8a1c498c98da56c7dc69696e
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07399775B2
Reaction notes
Loading…