Acetic Acid → Ethyl 2-(aminocarbonyl)-3-[4-(trimethylsilanylmethoxy)phenyl]acrylate

HRID 899020ノート

反応式

HRID 899020 の反応式
[CH3:1][Si:2]([CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)([CH3:4])[CH3:3].[CH3:15][CH2:16][O:17][C:18]([CH2:20][C:21]([NH2:23])=[O:22])=[O:19].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[NH2:23][C:21]([C:20](=[CH:11][C:10]1[CH:13]=[CH:14][C:7]([O:6][CH2:5][Si:2]([CH3:4])([CH3:3])[CH3:1])=[CH:8][CH:9]=1)[C:18]([O:17][CH2:16][CH3:15])=[O:19])=[O:22]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 238112Ethyl 2-carbamoylacetateHCID 565289644-Trimethylsilanylmethoxybenzaldehyde

生成物 1

HCID 69260375Ethyl 2-(aminocarbonyl)-3-[4-(trimethylsilanylmethoxy)phenyl]acrylate収率 37%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

4-(Trimethylsilanylmethoxy)benzaldehyde (obtained in step 1 of Example 1) (3 g, 0.015 mol) and ethyl malonate monoamide (2.1 g, 0.016 mol) in 10 ml of dry toluene in the presence of 0.24 ml of piperidine and 0.14 g of acetic acid are refluxed for 3 hours in a reactor equipped with Dean-Stark apparatus. The water formed is removed azeotropically. The mixture is cooled and the toluene is removed by distillation. The reaction mixture is taken up in 50 ml of diisopropyl ether. The organic phase is washed 3 times with water, dried over sodium sulfate and filtered, and the solvent is evaporated off under vacuum. The yellow gum obtained is crystallized from a diisopropyl ether/heptane mixture. 1.8 g (yield: 37%) of the derivative of Example 8 are obtained in the form of a pale yellow solid:

後処理

  1. customequipped with Dean-Stark apparatus
  2. customis removed azeotropically
  3. temperatureThe mixture is cooled
  4. customthe toluene is removed by distillation
  5. washThe organic phase is washed 3 times with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent is evaporated off under vacuum
  9. customThe yellow gum obtained
  10. customis crystallized from a diisopropyl ether/heptane mixture
  11. custom1.8 g (yield: 37%) of the derivative of Example 8 are obtained in the form of a pale yellow solid

出典と根拠

ORDレコード
ord-d0885b9d715f4db39b8c1380cf730a87
出典データセット
uspto-grants-2008_04
特許番号
US07354571B2

反応ノート

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