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

HRID 899020

반응식

HRID 899020 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-d0885b9d715f4db39b8c1380cf730a87
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354571B2

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