Hydrochloric Acid → Methyl 6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)-4-hexenoate

HRID 888327

Reaction equation

HRID 888327 reaction equation
C1(C)C=CC(S(O[CH2:11][CH:12]=[CH:13][C:14]([F:17])([F:16])[F:15])(=O)=O)=CC=1.[F:19][C:20]([F:32])([F:31])[CH2:21][CH2:22][S:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])(=[O:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[F:15][C:14]([F:17])([F:16])[CH:13]=[CH:12][CH2:11][CH:26]([S:23]([CH2:22][CH2:21][C:20]([F:19])([F:31])[F:32])(=[O:24])=[O:25])[C:27]([O:29][CH3:30])=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 536558394,4,4-Trifluoro-2-butenyl p-toluenesulfonateHCID 57425720Methyl 2-(3,3,3-trifluoropropylsulfonyl)acetate

Product 1

HCID 86642981Methyl 6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)-4-hexenoateYield 47.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2.4 g of 4,4,4-trifluoro-2-butenyl p-toluenesulfonate and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate in 50 ml of dimethyl sulfoxide, 1.2 g of potassium carbonate was added at room temperature and stirred at the same temperature for 16 hours. To the reaction mixture, 10% hydrochloric acid was added, followed by extraction 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 1.40 g of methyl 6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)-4-hexenoate (hereinafter referred to as the present compound (17)).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9a5c1b7fdfc49adb3b8f2411ba41995
Source dataset
uspto-grants-2012_08
Patent number
US08247595B2

Linked notes

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