Hydrochloric Acid → 6-Methyl-2-(3,3,3-trifluoropropylsulfonyl)-7-octynenitrile
Reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH:9]([CH3:12])[C:10]#[CH:11])(=O)=O.[F:13][C:14]([F:24])([F:23])[CH2:15][CH2:16][S:17]([CH2:20][C:21]#[N:22])(=[O:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[CH3:12][CH:9]([C:10]#[CH:11])[CH2:8][CH2:7][CH2:6][CH:20]([S:17]([CH2:16][CH2:15][C:14]([F:24])([F:13])[F:23])(=[O:19])=[O:18])[C:21]#[N:22]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 1.0 g of 4-methyl-5-hexynyl methanesulfonate and 1.1 g of (3,3,3-trifluoropropylsulfonyl)acetonitrile in 30 ml of dimethyl sulfoxide was added 0.7 g of potassium carbonate at room temperature. The reaction mixture was stirred at 60° C. for 2 days. The reaction mixture was allowed to stand to cool to nearly room temperature. To the reaction mixture was added 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.45 g of 6-methyl-2-(3,3,3-trifluoropropylsulfonyl)-7-octynenitrile (hereinafter referred to as the present compound (28)).
Workup
- temperatureto cool to nearly room temperature
- extractionextracted with ethyl acetate
- washThe organic layer was washed with a saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-15d67979df5441e292fb499fbfecbcaf
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247595B2
Reaction notes
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