Sodium hydride → Diethyl 2-(5-chloropentyl)-2-(4,4,5,5,5-pentafluoropentyl)malonate
Reaction equation
[F:1][C:2]([F:21])([C:17]([F:20])([F:19])[F:18])[CH2:3][CH2:4][CH2:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Cl:30]>CS(C)=O.O>[Cl:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:6]([CH2:5][CH2:4][CH2:3][C:2]([F:21])([F:1])[C:17]([F:18])([F:19])[F:20])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]([O:14][CH2:15][CH3:16])=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Diethyl 2-(4,4,5,5,5-pentafluoropentyl)malonate (3 g, 9.37 mmol) was dissolved in dimethyl sulfoxide (20 ml), and sodium hydride (60%, 525 mg, 13.11 mmol) was added to the resulting solution followed by stirring for 1 hour at room temperature. 5-Bromo-1-chloropentane (7.4 ml, 56.2 mmol) was added to the reaction mixture, followed by stirring for 1.5 hours at room temperature. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: dichloromethane/hexane=1/4) to give diethyl 2-(5-chloropentyl)-2-(4,4,5,5,5-pentafluoropentyl)malonate (3.3 g, Yield 83%) as a colorless oil.
Workup
- stirringby stirring for 1.5 hours at room temperature
- extractionextracted with ethyl acetate
- washwashed with water and saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- concentrationThe filtrate was concentrated under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography (eluent: dichloromethane/hexane=1/4)
Sources & evidence
- ORD record
- ord-bb84b16c6dea4a6c80a62702895d8f3b
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196081B2
Reaction notes
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