Hydrochloric Acid → HCID 59378482, compound

HRID 888333Notes

Reaction equation

CS(O[CH2:6][CH2:7][CH:8]([CH3:12])[CH2:9][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].[H-].[Na+].Cl>CS(C)=O>[CH3:12][CH:8]([CH2:9][C:10]#[CH:11])[CH2:7][CH2:6][CH:20]([S:17]([CH2:16][CH2:15][C:14]([F:13])([F:23])[F:24])(=[O:18])=[O:19])[C:21]#[N:22]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 1.0 g of 3-methyl-5-hexynyl methanesulfonate and 1.1 g of (3,3,3-trifluoropropylsulfonyl)acetonitrile in 30 ml of dimethyl sulfoxide was added 0.2 g of sodium hydride (60% in oil) at room temperature. The reaction mixture was stirred at 60° C. for 3 days and at 90° C. for 2 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 0.69 g of 5-methyl-2-(3,3,3-trifluoropropylsulfonyl)-7-octynenitrile (hereinafter referred to as the present compound (27)).

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-5d13701dae074f75927cda324b50c163
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247595B2

Reaction notes

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