Hydrochloric Acid → HCID 86642973, compound

HRID 888550Notes

Reaction equation

CS(O[CH2:6][CH2:7][CH:8]([S:13][CH3:14])[C:9]([F:12])([F:11])[F:10])(=O)=O.[F:15][C:16]([F:28])([F:27])[CH2:17][CH2:18][S:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])(=[O:21])=[O:20].[H-].[Na+].Cl>CS(C)=O>[F:12][C:9]([F:10])([F:11])[CH:8]([S:13][CH3:14])[CH2:7][CH2:6][CH:22]([S:19]([CH2:18][CH2:17][C:16]([F:27])([F:28])[F:15])(=[O:21])=[O:20])[C:23]([O:25][CH3:26])=[O:24]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5.0 g of 4,4,4-trifluoro-3-methylthio-butyl methanesulfonate and 4.6 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate in 50 ml of dimethyl sulfoxide was added 0.8 g of sodium hydride (60% in oil) at room temperature. The reaction mixture was heated to 60° C., stirred at the same temperature for 5 days, and then 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 2.00 g of methyl 6,6,6-trifluoro-5-methylthio-2-(3,3,3-trifluoropropylsulfonyl)hexanoate (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-de7d0a66d73b4714b318545c2053aeb1
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247612B2

Reaction notes

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