Toluene → Diethyl 2-[[4-(methylthio)phenyl]methylene]propanedioate

HRID 231202

反応式

HRID 231202 の反応式
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:11]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C1(C)C=CC=CC=1>N1CCCCC1.C(O)(=O)C.O>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5][CH:4]=1

参加物

7

反応物 3

HCID 1140TolueneHCID 7761Diethyl MalonateHCID 769854-(Methylthio)benzaldehyde

生成物 1

HCID 13221107Diethyl 2-[[4-(methylthio)phenyl]methylene]propanedioate

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 8082Piperidine触媒HCID 962Water溶媒

実験手順

4-(Methylthio)Benzaldehyde (3.04 g, .02 mol), diethyl malonate (3.20 g. .02 mol), toluene (25 mL), piperidine (4 drops) and acetic acid (2 drops) are mixed and heated at reflux for 2 hours with the water formed being removed azeotropically. The solution is cooled and 25 mL of water added stirring. After separation of the layers, the toluene is evaporated from the organic layer to yield the product, diethyl 2-[[4-(methylthio)phenyl]methylene]propanedioate, in essentially quantitative yield. When dissolved in methylene chloride, the product has an absorption maximum (λmax) at 330 nm in the ultraviolet absorption spectrum. The identity of the product is confirmed by mass spectroscopy analysis.

後処理

  1. temperatureheated
  2. customformed
  3. custombeing removed azeotropically
  4. temperatureThe solution is cooled
  5. addition25 mL of water added
  6. customAfter separation of the layers
  7. customthe toluene is evaporated from the organic layer

出典と根拠

ORDレコード
ord-77b5d0c0f78b4a40a24f9e1c86dcdda1
出典データセット
uspto-grants-1989_07
特許番号
US04845188

関連ノート

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