Hydrochloric Acid → 2-(4,4,5,5,5-Pentafluoropentyl)-2-(3,3,3-trifluoropropyl)malononitrile
Reaction equation
FC(F)(F)S(O[CH2:7][CH2:8][CH2:9][C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])(=O)=O.[F:19][C:20]([F:29])([F:28])[CH2:21][CH2:22][CH:23]([C:26]#[N:27])[C:24]#[N:25].C(=O)([O-])[O-].[K+].[K+].Cl>COCCOC>[F:16][C:10]([F:15])([C:11]([F:12])([F:13])[F:14])[CH2:9][CH2:8][CH2:7][C:23]([CH2:22][CH2:21][C:20]([F:19])([F:28])[F:29])([C:24]#[N:25])[C:26]#[N:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To 10 ml of ethylene glycol dimethyl ether, 6.2 g of 4,4,5,5,5-pentafluoropentyl trifluoromethanesulfonate, 1.6 g of 2-(3,3,3-trifluoropropyl)malononitrile and 1.4 g of potassium carbonate were added and the mixture was stirred at room temperature for 5 hours. Thereafter, dilute hydrochloric acid was added to the reaction mixture and the mixture was extracted with t-butyl methyl ether. The organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.65 g of 2-(4,4,5,5,5-pentafluoropentyl)-2-(3,3,3-trifluoropropyl)malononitrile (hereinafter, referred to as the present compound (89)).
Workup
- extractionthe mixture was extracted with t-butyl methyl ether
- washThe organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d282432eb6f94f90a9b13acc5b63d3c3
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07662402B2
Reaction notes
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