Hydrochloric Acid → HCID 59378486, compound

HRID 888335Notes

Reaction equation

CS(O[CH2:6][CH2:7][CH:8]([CH2:12][CH3:13])[CH2:9][C:10]#[CH:11])(=O)=O.[F:14][C:15]([F:25])([F:24])[CH2:16][CH2:17][S:18]([CH2:21][C:22]#[N:23])(=[O:20])=[O:19].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[CH2:7]([CH:8]([CH2:9][C:10]#[CH:11])[CH2:12][CH2:13][CH:21]([S:18]([CH2:17][CH2:16][C:15]([F:14])([F:24])[F:25])(=[O:19])=[O:20])[C:22]#[N:23])[CH3:6]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 0.7 g of 3-ethyl-5-hexynyl methanesulfonate and 0.7 g of (3,3,3-trifluoropropylsulfonyl)acetonitrile in 20 ml of dimethyl sulfoxide was added 0.5 g of potassium carbonate at room temperature. The reaction mixture was stirred at 60° C. for 20 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 0.40 g of 5-ethyl-2-(3,3,3-trifluoropropylsulfonyl)-7-octynenitrile (hereinafter referred to as the present compound (29)).

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-35a1caaa43604e7986deb07ee7454bb9
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247595B2

Reaction notes

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