Ethyl cyanoacetate → HCID 69507081、化合物

HRID 1768419ノート

反応式

HRID 1768419 の反応式
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]

参加物

9

反応物 6

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

生成物 1

HCID 69507081HCID 69507081、化合物収率 0.9%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1140Toluene溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0d28738b75814e69ba81ae250129489e
出典データセット
uspto-grants-2007_06
特許番号
US07235674B2

反応ノート

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