Methyl-6-methoxy-2-indolecarboxylate → 6-methoxy-2-methyl-1H-indole

HRID 252512ノート

反応式

HRID 252512 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18](OC)=O)[NH:15]2)=[CH:11][CH:10]=1>O1CCOCC1>[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([CH3:18])[NH:15]2)=[CH:11][CH:10]=1

参加物

4

反応物 2

HCID 688173Methyl-6-methoxy-2-indolecarboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 108447096-methoxy-2-methyl-1H-indole収率 61%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

To a suspension of LiAlH4 (7.6 g, 0.2 mol) in dioxane (100 mL) is added dropwise a solution of methyl 6-methoxy-1H-indole-2-carboxylate (8.2 g, 0.04 mol) in dioxane (50 mL) at 0° C. After the addition, the mixture is stirred at room temperature for 1 h and then heated at reflux for 5 h. After cooling to 0° C., the reaction is quenched by water (dropwise) and then 15% aqueous NaOH. After stirring at room temperature for 1 h, the mixture is filtered through Celite. The solid is washed with a large amount of EtOAc. The solvent is washed with brine, dried over Na2SO4 and evaporated under vacuum. The residue is purified by flash column chromatography on silica gel using EtOAc/petroleum ether (1/5) as eluent to yield 61% of 6-methoxy-2-methyl-1H-indole.

後処理

  1. additionAfter the addition
  2. temperatureheated
  3. temperatureat reflux for 5 h
  4. temperatureAfter cooling to 0° C.
  5. customthe reaction is quenched by water (dropwise) and then 15% aqueous NaOH
  6. stirringAfter stirring at room temperature for 1 h
  7. filtrationthe mixture is filtered through Celite
  8. washThe solid is washed with a large amount of EtOAc
  9. washThe solvent is washed with brine
  10. dry with materialdried over Na2SO4
  11. customevaporated under vacuum
  12. customThe residue is purified by flash column chromatography on silica gel

出典と根拠

ORDレコード
ord-abcfa7f9cad24899a50111778ccc839a
出典データセット
uspto-grants-2011_01
特許番号
US07868037B2

反応ノート

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