Water → 2-(5-Fluoropentyl)-2-(3,3,3-trifluoropropyl)malononitrile
Reaction equation
C(N(S(F)(F)[F:7])CC)C.O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([CH2:21][CH2:22][C:23]([F:26])([F:25])[F:24])([C:19]#[N:20])[C:17]#[N:18].O>C(Cl)(Cl)Cl>[F:7][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([CH2:21][CH2:22][C:23]([F:26])([F:25])[F:24])([C:19]#[N:20])[C:17]#[N:18]Participants
Procedure
0.29 g of diethylaminosulfur trifluoride was dissolved in 5 ml of chloroform and thereto was added dropwise at 0° C. 0.40 g of 2-(5-hydroxypentyl)-2-(3,3,3-trifluoropropyl)malononitrile dissolved in 3 ml of chloroform. The mixture was stirred at room temperature for 9 hours. Thereafter, water was added to the reaction mixture, followed by extraction with methyl tert-butyl 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 0.12 g of 2-(5-fluoropentyl)-2-(3,3,3-trifluoropropyl)malononitrile (hereinafter, referred to as the present compound (55)).
Workup
- additionwas added dropwise at 0° C
- extractionfollowed by extraction with methyl tert-butyl 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-72167660c5b94f48aa76aacf57b3c998
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07662402B2
Reaction notes
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