Dimethyl Sulfoxide → Diethyl methyl(4-nitrophenyl)propanedioate
Reaction equation
C[CH2:2][CH:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.[CH3:25]S(C)=O>>[CH3:2][C:3]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)([C:4]([O:6][CH2:7][CH3:25])=[O:5])[C:8]([O:10][CH2:11][CH3:12])=[O:9]Participants
Procedure
Diethyl methyl malonate (6.17 g, 35.4 mmol) was added to a stirred solution of sodium hydride (1.63 g, 42.5 mmol, 60%) in DMSO (50 ml) and stirred for 1 h at room temperature. 1-Fluoro-4-nitrobenzene (5.00 g, 35.4 mmol) was added dropwise to the reaction mixture and stirred for 6 h at room temperature. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with diethyl ether. The separated organic layer was washed with brine solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the crude product. Purified by column chromatography over silica gel (60-120 mesh) using 20% ethyl acetate in petroleum ether as eluent afford 8.20 g (78.8%) of diethyl 2-methyl-2-(4-nitrophenyl)malonate as an oil.
Workup
- stirringstirred for 6 h at room temperature
- customThe reaction mixture was quenched with saturated ammonium chloride solution
- extractionextracted with diethyl ether
- washThe separated organic layer was washed with brine solution
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto afford the crude product
- customPurified by column chromatography over silica gel (60-120 mesh)
Sources & evidence
- ORD record
- ord-a7889a8e5ebd47918d8f7563c3c5b19b
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518948B2
Reaction notes
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