Ethyl cyanoacetate → HCID 69507081, 화합물
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
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
- customThe solvent was evaporated
- stirringthe mixture was stirred at room temperature for 0.5 h
- temperaturethe mixture was refluxed for 2 h
- customThe solvent was evaporated
- customthe residue was purified by chromatography on silica gel with ethyl acetate and hexane (1:2) as eluant
출처 및 근거
- ORD 기록
- ord-0d28738b75814e69ba81ae250129489e
- 출처 데이터셋
- uspto-grants-2007_06
- 특허 번호
- US07235674B2
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