Hydrochloric Acid → HCID 86642983, compound

HRID 888329Notes

Reaction equation

HRID 888329 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[F:8][C:9]([F:21])([F:20])[CH2:10][CH2:11][S:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:14])=[O:13].[H-].[Na+].Cl>CS(C)=O>[F:21][C:9]([F:8])([F:20])[CH2:10][CH2:11][S:12]([CH:15]([CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH2:2])[C:16]([O:18][CH3:19])=[O:17])(=[O:13])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 759066-Bromo-1-hexeneHCID 57425720Methyl 2-(3,3,3-trifluoropropylsulfonyl)acetate

Product 1

HCID 86642983HCID 86642983, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2.0 g of 6-bromo-1-hexene and 2.9 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate in 50 ml of dimethyl sulfoxide, 0.5 g of sodium hydride (60% in oil) was added at room temperature. The mixture was heated to 60° C., stirred for 4 hours, and then allowed to stand near room temperature. 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 3.10 g of methyl 2-(3,3,3-trifluoropropylsulfonyl)-7-octenoate (hereinafter referred to as the present compound (20)).

Workup

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

Sources & evidence

ORD record
ord-4ce8cad8df7040efb66302c0450b9e6b
Source dataset
uspto-grants-2012_08
Patent number
US08247595B2

Reaction notes

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