Hydrochloric Acid → HCID 86642972, compound

HRID 888549Notes

Reaction equation

HRID 888549 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH:13]([O:18][CH3:19])[C:14]([F:17])([F:16])[F:15])(=O)=O)=CC=1.[F:21][C:22]([F:34])([F:33])[CH2:23][CH2:24][S:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])(=[O:27])=[O:26].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[F:17][C:14]([F:15])([F:16])[CH:13]([O:18][CH3:19])[CH2:12][CH2:11][CH:28]([S:25]([CH2:24][CH2:23][C:22]([F:33])([F:34])[F:21])(=[O:27])=[O:26])[C:29]([O:31][CH3:32])=[O:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 57425720Methyl 2-(3,3,3-trifluoropropylsulfonyl)acetateHCID 59378436HCID 59378436, compound

Product 1

HCID 86642972HCID 86642972, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1.0 g of 4,4,4-trifluoro-3-methoxy-butyl p-toluenesulfonate and 0.8 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate in 50 ml of dimethyl sulfoxide was added 0.4 g of potassium carbonate at room temperature, and the stirred at room temperature for 4 days. 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 0.62 g of methyl 6,6,6-trifluoro-5-methoxy-2-(3,3,3-trifluoropropylsulfonyl)hexanoate (hereinafter referred to as the present compound (24)).

Workup

  1. temperatureThe reaction mixture was heated to 60° C.
  2. stirringstirred at the same temperature for 20 hours
  3. temperatureto cool to nearly room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b75a53a3243348569f72f26d3580d315
Source dataset
uspto-grants-2012_08
Patent number
US08247612B2

Reaction notes

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