Hydrochloric Acid → 2-(3,3,3-Trifluoropropylsulfonyl)-9-decynenitrile

HRID 888332

Reaction equation

C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])(=O)=O)=CC=1.[F:20][C:21]([F:31])([F:30])[CH2:22][CH2:23][S:24]([CH2:27][C:28]#[N:29])(=[O:26])=[O:25].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[F:31][C:21]([F:20])([F:30])[CH2:22][CH2:23][S:24]([CH:27]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]#[CH:11])[C:28]#[N:29])(=[O:25])=[O:26]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1.0 g of 7-octynyl p-toluenesulfonate and 0.7 g of (3,3,3-trifluoropropylsulfonyl)acetonitrile in 30 ml of dimethyl sulfoxide was added 0.5 g of potassium carbonate at room temperature. The reaction mixture was stirred at room temperature for 2 hours, at 60° C. for 2 hours, and then at 90° C. for 6 hours. 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 0.28 g of 2-(3,3,3-trifluoropropylsulfonyl)-9-decynenitrile (hereinafter referred to as the present compound (25)).

Workup

waitat 90° C. for 6 hours
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-7cf2a36cffb54379bc2be9cc2145193d
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247595B2

Linked notes

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