alpha,alpha,alpha-Trifluoro-3-nitro-o-xylene → [1-(4-Methoxyphenyl)-2-[2-nitro-6-(trifluoromethyl)phenyl]ethyl]propanedioic acid, dimethyl ester

HRID 344787ノート

反応式

HRID 344787 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][C:20]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][C:21]=1[N+:30]([O-:32])=[O:31].[CH3:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([CH:41]=[C:42]([C:47]([O:49][CH3:50])=[O:48])[C:43]([O:45][CH3:46])=[O:44])=[CH:37][CH:36]=1>O1CCCC1>[CH3:33][O:34][C:35]1[CH:36]=[CH:37][C:38]([CH:41]([CH:42]([C:47]([O:49][CH3:50])=[O:48])[C:43]([O:45][CH3:46])=[O:44])[CH2:19][C:20]2[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][C:21]=2[N+:30]([O-:32])=[O:31])=[CH:39][CH:40]=1

参加物

5

反応物 3

HCID 81171alpha,alpha,alpha-Trifluoro-3-nitro-o-xyleneHCID 100478Dimethyl (p-methoxybenzylidene)malonateHCID 2724141Tetrabutylammonium Fluoride

生成物 1

HCID 14156192[1-(4-Methoxyphenyl)-2-[2-nitro-6-(trifluoromethyl)phenyl]ethyl]propanedioic acid, dimethyl ester収率 90.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a vigorously stirring mixture of molecular sieves (5.25 g) and tetra-n-butylammonium fluoride (0.882 g) was added dry tetrahydrofuran (10 ml) at 0° C. 2-Methyl-1-nitro-3-(trifluoromethyl)benzene (0.425 ml; 2.8 mmol) was added to the suspension followed by the addition of a solution of 2-[(4-methoxyphenyl)methylene]propanedioic acid, dimethyl ester (0.44 g; 1.75 mmol) in 5 ml of tetrahydrofuran. After 30 minutes of 0° C. the reaction was brought to room temperature and stirred for another 20 minutes. The reaction was quenched with 30% acetic acid until a light yellow color was observed and thereafter was diluted with 45 ml of ethyl ether, filtered and washed twice with 30 ml of ethyl ether. The combined organic solution was washed with sodium hydrogen carbonate and dried over magnesium sulfate. Concentration and chromatography provided 0.72 g of the title compound as a foam.

後処理

  1. stirringstirred for another 20 minutes
  2. customThe reaction was quenched with 30% acetic acid until a light yellow color
  3. additionwas diluted with 45 ml of ethyl ether
  4. filtrationfiltered
  5. washwashed twice with 30 ml of ethyl ether
  6. washThe combined organic solution was washed with sodium hydrogen carbonate
  7. dry with materialdried over magnesium sulfate
  8. concentrationConcentration and chromatography

出典と根拠

ORDレコード
ord-45659c1bed634b0f93a3e63c11ffa472
出典データセット
uspto-grants-1991_10
特許番号
US05053504

反応ノート

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