Hydrochloric Acid → Methyl 6,6,6-trifluoro-5-methyl-2-(3,3,3-trifluoropropylsulfonyl)hexanoate

HRID 888542Notes

Reaction equation

C1(C)C=CC(S(O[CH2:11][CH2:12][CH:13]([CH3:18])[C:14]([F:17])([F:16])[F:15])(=O)=O)=CC=1.[F:20][C:21]([F:33])([F:32])[CH2:22][CH2:23][S:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])(=[O:26])=[O:25].[H-].[Na+].Cl>CS(C)=O>[F:15][C:14]([F:17])([F:16])[CH:13]([CH3:18])[CH2:12][CH2:11][CH:27]([S:24]([CH2:23][CH2:22][C:21]([F:20])([F:32])[F:33])(=[O:25])=[O:26])[C:28]([O:30][CH3:31])=[O:29]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2.0 g of 4,4,4-trifluoro-3-methylbutyl p-toluenesulfonate and 1.6 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate in 50 ml of dimethyl sulfoxide was added 0.3 g of sodium hydride (60% in oil) at room temperature. The reaction mixture was heated to 60° C., stirred at the same temperature for 20 hours, 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 0.83 g of methyl 6,6,6-trifluoro-5-methyl-2-(3,3,3-trifluoropropylsulfonyl)hexanoate (hereinafter referred to as the present compound (1)).

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-6d098734684948b88a35eed7569b1aa0
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247612B2

Reaction notes

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