Hydrochloric Acid → Methyl 6,6-dimethyl-5-trifluoromethyl-2-(3,3,3-trifluoropropylsulfonyl)heptanoate

HRID 888544Notes

Reaction equation

C1(C)C=CC(S(O[CH2:11][CH2:12][CH:13]([C:18]([F:21])([F:20])[F:19])[C:14]([CH3:17])([CH3:16])[CH3:15])(=O)=O)=CC=1.[F:23][C:24]([F:36])([F:35])[CH2:25][CH2:26][S:27]([CH2:30][C:31]([O:33][CH3:34])=[O:32])(=[O:29])=[O:28].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[CH3:17][C:14]([CH3:15])([CH3:16])[CH:13]([C:18]([F:19])([F:20])[F:21])[CH2:12][CH2:11][CH:30]([S:27]([CH2:26][CH2:25][C:24]([F:35])([F:36])[F:23])(=[O:29])=[O:28])[C:31]([O:33][CH3:34])=[O:32]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2.9 g of 4,4-dimethyl-3-(trifluoromethyl)pentyl p-toluenesulfonate and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate in 30 ml of dimethyl sulfoxide was added 1.2 g of potassium carbonate at room temperature. The reaction mixture was heated to 90° C., stirred at the same temperature for 6 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 2.00 g of methyl 6,6-dimethyl-5-trifluoromethyl-2-(3,3,3-trifluoropropylsulfonyl)heptanoate (hereinafter referred to as the present compound (7)).

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-59c15ecbba334c7e9ec4a4461e58111e
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247612B2

Reaction notes

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