Ethyl cyanoacetate → HCID 69507081, 화합물

HRID 1744442노트

반응식

HRID 1744442 반응식
COC1C=C(C=CC=1)C=O.C(CC(OCC)=O)#N.N1CCCCC1.[OH:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:27]=1[CH:28]=[CH:29][NH:30]2.[H-].[Na+].C([O:39][C:40](=O)[C:41]([C:51]#[N:52])=[CH:42][C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([O:49][CH3:50])[CH:44]=1)C>C(O)C.C1(C)C=CC=CC=1>[C:51]([CH:41]1[C:42]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([O:49][CH3:50])[CH:44]=2)=[C:34]2[C:26](=[C:27]3[CH:28]=[CH:29][N:30]=[C:31]3[CH:32]=[CH:33]2)[O:25][C:40]1=[O:39])#[N:52]

참가 물질

9

반응물 6

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 115693-MethoxybenzaldehydeHCID 24758Sodium hydrideHCID 754211H-indol-4-olHCID 3674973-(3-Methoxyphenyl)-2-cyano-acrylic acid ethyl ester

생성물 1

HCID 69507081HCID 69507081, 화합물수율 0.9%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 1140Toluene용매2회

실험 절차

To a solution of 3-methoxybenzaldehyde (2.0 g, 15.0 mmol) and ethyl cyanoacetate (1.56 mL, 15.0 mmol) in ethanol (10 mL) was added piperidine (0.73 ml, 7.5 mmol). The mixture was stirred at room temperature overnight. The solvent was evaporated and the crude oil was used for the next step. To a solution of 4-hydroxyindole (266.3 mg, 2 mmol) in toluene (5 mL) was added sodium hydride (100 mg, 2.5 mmol, 60%) and the mixture was stirred at room temperature for 0.5 h. To the mixture was added the 3-(3-methoxy-phenyl)-2-cyano-acrylic acid ethyl ester (462.5 mg, 2 mmol) dissolved in toluene (1 mL), then the mixture was refluxed for 2 h. The solvent was evaporated and the residue was purified by chromatography on silica gel with ethyl acetate and hexane (1:2) as eluant, yielding 6 mg (0.9%) the title compound. 1H NMR (CDCl3): 8.67 (brs, 1H), 7.54-7.48 (m, 1H), 7.35-7.31 (m, 2H), 7.15-7.01 (m, 5H), 3.88 (s, 3H).

후처리

  1. customThe solvent was evaporated
  2. stirringthe mixture was stirred at room temperature for 0.5 h
  3. temperaturethe mixture was refluxed for 2 h
  4. customThe solvent was evaporated
  5. customthe residue was purified by chromatography on silica gel with ethyl acetate and hexane (1:2) as eluant

출처 및 근거

ORD 기록
ord-4650369ad23f4182b9133136d8e5c326
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015328B2

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