3,4-dihydro-2H-pyran → 2-Acetyl-5-ethyl-7,7-dimethyl-1-(tetrahydro-pyran-2-yl)-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

HRID 1181578ノート

反応式

HRID 1181578 の反応式
[C:1]([C:4]1[NH:20][C:7]2=[CH:8][C:9]3[C:10]([CH3:19])([CH3:18])[C:11](=[O:17])[N:12]([CH2:15][CH3:16])[C:13]=3[CH:14]=[C:6]2[N:5]=1)(=[O:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:33]1[CH:38]=[CH:37][CH2:36][CH2:35][CH2:34]1>ClCCl>[C:1]([C:4]1[N:20]([CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38][O:33]2)[C:7]2=[CH:8][C:9]3[C:10]([CH3:19])([CH3:18])[C:11](=[O:17])[N:12]([CH2:15][CH3:16])[C:13]=3[CH:14]=[C:6]2[N:5]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 694026672-Acetyl-5-ethyl-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

生成物 1

HCID 694016542-Acetyl-5-ethyl-7,7-dimethyl-1-(tetrahydro-pyran-2-yl)-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one収率 44.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-Acetyl-5-ethyl-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (11.7 g, 43.1 mmol) and p-toluenesulfonic acid monohydrate (0.82 g, 4.3 mmol) were dissolved in dichloromethane (200 mL). To this solution 3,4-dihydro-2H-pyrane (4.81 g, 56 mmol) was added and the mixture stirred at reflux for 24 h. The mixture was filtered, the filtrate washed with water (2×100 mL), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography on silica (dichloromethane/methanol 93:3) yielding 6.8 g (44%) of a light yellow solid.

後処理

  1. temperatureat reflux for 24 h
  2. filtrationThe mixture was filtered
  3. washthe filtrate washed with water (2×100 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica (dichloromethane/methanol 93:3)

出典と根拠

ORDレコード
ord-70187116a86941a9925acf830b1c0e6d
出典データセット
uspto-grants-2007_10
特許番号
US07285569B2

反応ノート

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