Methyl acetoacetate → Diisopropyl Ether

HRID 2054704노트

반응식

HRID 2054704 반응식
[N:1]1[O:2][N:3]=[C:4]2[C:9]([CH:10]=O)=[CH:8][CH:7]=[CH:6][C:5]=12.[C:12]([O:18][CH3:19])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].N1CC[CH2:23][CH2:22][CH2:21]1>C(OC(C)C)(C)C.C(O)(=O)C.O>[CH3:19][O:18][C:12](=[O:17])[C:13]([C:14](=[O:15])[CH3:16])=[CH:10][C:9]1[C:4]2=[N:3][O:2][N:1]=[C:5]2[CH:6]=[CH:7][CH:8]=1.[CH:22]([O:15][CH:14]([CH3:16])[CH3:13])([CH3:23])[CH3:21]

참가 물질

8

반응물 3

HCID 7757Methyl acetoacetate3회HCID 8082Piperidine3회HCID 102908732,1,3-Benzoxadiazole-4-carbaldehyde4회

생성물 2

HCID 7914Diisopropyl EtherHCID 534332132-Acetyl-3-benzofurazan-4-yl-acrylic acid methyl ester

시약·촉매·용매 3

HCID 176Acetic Acid용매3회HCID 962Water용매HCID 7914Diisopropyl Ether용매2회

실험 절차

In the first step, 2,1,3-benzoxadiazole-4-carboxaldehyde is reacted with methyl acetoacetate in the presence of acetic acid and piperidine in diisopropyl ether. The reaction is carried out in diisopropyl ether under reflux with simultaneous removal of water formed during the reaction. Removal of the water from the reaction mixture enables the reaction to proceed at a faster rate. The reaction is completed at the end of theoretical amount of water removal from the reaction mixture. The completion of the reaction is determined by qualitative HPLC analysis. In this reaction methyl acetoacetate 0.9 to 1.1 mol is used for every 1.0 mol of 2,1,3-benzoxadiazole-4-carboxaldehyde, preferably 0.95 to 1.0 mol methyl acetoacetate is used for every 1.0 mol of 2,1,3-benzoxadiazole-4-carboxaldehyde. Acetic acid and piperidine are used in catalytic amount, preferably acetic acid 0.25 to 0.30 mol and piperidine 0.08 to 0.06 mol is used for every 1.0 mol of 2,1,3-benzoxadiazole-4-carboxaldehyde. This reaction goes to completion after 8 to 12 hr at reflux. The reaction mixture is then washed with dilute hydrochloric acid, followed by dilute sodium bicarbonate solution and followed by water. The crude product 2-acetyl-3-benzofurazan-4-yl-acrylic acid methyl ester is then obtained by distillation of diisopropyl ether under vacuum.

후처리

  1. customformed during the reaction
  2. customRemoval of the water from the reaction mixture
  3. customthe reaction
  4. customThe reaction is completed at the end of theoretical amount of water removal from the reaction mixture
  5. temperatureat reflux
  6. washThe reaction mixture is then washed with dilute hydrochloric acid

출처 및 근거

ORD 기록
ord-a4e7f0d9e46844bd9e5857cfe42c9a77
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07329756B2

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