Hydrochloric Acid → Methyl 5-trifluoromethyl-2-(3,3,3-trifluoropropylsulfonyl)-4-heptenoate

HRID 888338Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3.0 g of 3-trifluoromethyl-2-pentenyl p-toluenesulfonate and 2.3 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate in 50 ml of N,N-dimethylformamide was added 0.4 g of sodium hydride (60% in oil) at room temperature. The reaction mixture was stirred at the same temperature for 10 hours, at 60° C. for 6 hours and then at 90° C. for 1 hour. The reaction mixture was 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 1.86 μg of methyl 5-trifluoromethyl-2-(3,3,3-trifluoropropylsulfonyl)-4-heptenoate (hereinafter referred to as the present compound (36)) as a mixture of (E) and (Z) isomers.

Workup

waitat 90° C. for 1 hour
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-b5e32633a8a6414fa5be889a91a456fd
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247595B2

Reaction notes

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