Dimethyl Sulfoxide → Diethyl methyl(4-nitrophenyl)propanedioate

HRID 2176905Notes

Reaction equation

HRID 2176905 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

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 5088009HCID 5088009, compound

Product 1

HCID 12380744Diethyl methyl(4-nitrophenyl)propanedioateYield 78.8%

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

  1. stirringstirred for 6 h at room temperature
  2. customThe reaction mixture was quenched with saturated ammonium chloride solution
  3. extractionextracted with diethyl ether
  4. washThe separated organic layer was washed with brine solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford the crude product
  9. customPurified by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-7887fe98730d40278be93d29d9f4a876
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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