Dimethyl Sulfoxide → Diethyl methyl(4-nitrophenyl)propanedioate

HRID 1896268ノート

反応式

HRID 1896268 の反応式
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]

参加物

5

反応物 4

HCID 679Dimethyl SulfoxideHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 5088009HCID 5088009、化合物

生成物 1

HCID 12380744Diethyl methyl(4-nitrophenyl)propanedioate収率 78.8%

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a7889a8e5ebd47918d8f7563c3c5b19b
出典データセット
uspto-grants-2013_08
特許番号
US08518948B2

反応ノート

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