Ammonium Chloride → 4-Cyano-4-(5-cyano-2-thienyl)-5-methylhexanol
Reaction equation
[C:1]([C:3]([C:18]1[S:22][C:21]([C:23]#[N:24])=[CH:20][CH:19]=1)([CH:15]([CH3:17])[CH3:16])[CH2:4][CH2:5][CH2:6][O:7][Si](C(C)(C)C)(C)C)#[N:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1.[Cl-].[Na+].O>[C:1]([C:3]([C:18]1[S:22][C:21]([C:23]#[N:24])=[CH:20][CH:19]=1)([CH:15]([CH3:17])[CH3:16])[CH2:4][CH2:5][CH2:6][OH:7])#[N:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
[4-Cyano-5-methyl-4-(2-cyano-5-thienyl)hexyloxy]-t-butyldimethylsilane, 452 mg 1.25 mmol, was dissolved in 10 ml tetrahydrofuran and cooled at 0° C. A solution of 1 M tetrabutylammonium fluoride in tetrahydrofuran 1.38 ml was added dropwise thereto, and then the temperature was raised to room temperature. Aqueous saturated ammonium chloride and brine were added to the reaction mixture which was then extracted with ether. The organic layer was washed with brine, dried over magnesium sulfate anhydride, and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 273 mg 1.10 mmol, 87.9%, was obtained as a yellow syrup.
Workup
- temperaturethe temperature was raised to room temperature
- extractionwas then extracted with ether
- washThe organic layer was washed with brine
- dry with materialdried over magnesium sulfate anhydride
- customevaporated
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 273 mg 1.10 mmol, 87.9%
- customwas obtained as a yellow syrup
Sources & evidence
- ORD record
- ord-e55cd9e6944d4396a9182eba99044124
- Source dataset
- uspto-grants-2004_05
- Patent number
- US06737425B1
Reaction notes
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