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Dimethyl Sulfoxide → Methyl 2-(2-chloro-4-nitrophenyl)acetate

HRID 1019730
ノート
印刷プレビュー

反応式

HRID 1019730 の反応式
[CH3:1][O:2][C:3](=[O:19])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[Cl:18])C(OC)=O.[Cl-].[Na+].CS(C)=O.O>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[Cl:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 962Water2 回HCID 5234Sodium ChlorideHCID 11414995Dimethyl 2-(2-chloro-4-nitrophenyl)malonate

生成物 1

HCID 21876245Methyl 2-(2-chloro-4-nitrophenyl)acetate収率 60.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate
溶媒

反応条件

温度
110 °C

実験手順

2-(2-Chloro-4-nitro-phenyl)-malonic acid dimethyl ester (6.0 g, 20.9 mmol) and sodium chloride (2.2 g, 37.6 mmol) were added to a mixture of DMSO (100 mL) and water (0.38 mL, 20.9 mmol) and the reaction mixture was heated for 8 hours at 110° C. The reaction mixture was cooled to RT and poured into water (500 mL). EtOAc (200 mL) was added to the mixture which was then stirred for 15 minutes. The separated aqueous phase was extracted with EtOAc (100 mL). The combined organic extracts were washed with brine (100 mL), dried (Na2SO4) and the solvents removed under reduced pressure. The residue was purified by column chromatography on neutral silica gel using 3-6% EtOAc in hexane to give the title compound (2.9 g, 60%).

後処理

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionThe separated aqueous phase was extracted with EtOAc (100 mL)
  3. washThe combined organic extracts were washed with brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. customthe solvents removed under reduced pressure
  6. customThe residue was purified by column chromatography on neutral silica gel using 3-6% EtOAc in hexane

出典と根拠

ORDレコード
ord-4966bc27cb0843529b9b5968715d6a69
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08716287B2

反応ノート

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