Potassium Carbonate → 2-Methyl-4-trifluoromethylsulfanyl-2-(2-trifluoromethylsulfanyl-ethanesulfonyl)-butyronitrile

HRID 80410Notes

Reaction equation

HRID 80410 reaction equation
[F:1][C:2]([S:5][CH2:6][CH2:7][S:8]([CH2:11][C:12]#[N:13])(=[O:10])=[O:9])([F:4])[F:3].[F:14][C:15]([S:18][CH2:19][CH2:20]OS(C(F)(F)F)(=O)=O)([F:17])[F:16].[C:29]([O-])([O-])=O.[K+].[K+]>COCCOC.O>[CH3:29][C:11]([S:8]([CH2:7][CH2:6][S:5][C:2]([F:1])([F:4])[F:3])(=[O:9])=[O:10])([CH2:20][CH2:19][S:18][C:15]([F:17])([F:16])[F:14])[C:12]#[N:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 252420282-(Trifluoromethylthio)ethyl TrifluoromethanesulfonateHCID 86673275(2-Trifluoromethylsulfanyl-ethanesulfonyl)-acetonitrile

Product 1

HCID 866732742-Methyl-4-trifluoromethylsulfanyl-2-(2-trifluoromethylsulfanyl-ethanesulfonyl)-butyronitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (2-trifluoromethylsulfanyl-ethanesulfonyl)-acetonitrile (190 mg, 0.81 mmol), trifluoro-methanesulfonic acid 2-trifluoromethylsulfanyl-ethyl ester (340 mg, 1.22 mmol) and K2CO3 (340 mg, 2.44 mmol) in 1,2-dimethoxyethane (10 mL) was stirred under nitrogen at room temperature overnight. The reaction mixture was diluted with H2O (40 mL) and extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with saturated aqueous NaCl solution, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography (SiO2, gradient of EtOAc/cyclohexane) to afford compound II-26 (20 mg, 7%).

Workup

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. washThe combined organic extracts were washed with saturated aqueous NaCl solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (SiO2, gradient of EtOAc/cyclohexane)
  6. customto afford compound

Sources & evidence

ORD record
ord-b9c21e2525bb471e8f7024d02c8f9b7d
Source dataset
uspto-grants-2014_09
Patent number
US08846569B2

Reaction notes

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