1-benzyl-5-benzyloxy-1H-indole → 1H-Indol-5-ol, 1-(phenylmethyl)-

HRID 854502ノート

反応式

HRID 854502 の反応式
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]CC3C=CC=CC=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd]>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

3

反応物 1

HCID 120956361-benzyl-5-benzyloxy-1H-indole

生成物 1

HCID 107754621H-Indol-5-ol, 1-(phenylmethyl)-収率 63.2%

試薬・触媒・溶媒 1

HCID 23938Palladium触媒2 回

実験手順

A slurry of 0.98 g (3.12 mmol) 1-benzyl-5-benzyloxy-1H-indole, 0.20 g 20% Palladium on carbon, and 1.51 g (24 mmol) NH4CHO was heated to reflux with stirring for 3 days. The reaction was allowed to cool and an additional 0.20 g 20% Palladium on carbon and 1.33 g NH4CHO was added. The reaction was refluxed for an additional 24 hours upon which time the reaction was complete by TLC. The reaction was filtered through paper and concentrated. The residue was chromatographed on silica using 25–40% EtOAc-hexane to afford 0.44 g 1-benzyl-5-hydroxy-1H-indole as a solid.

後処理

  1. temperatureto reflux
  2. temperatureto cool
  3. temperatureThe reaction was refluxed for an additional 24 hours upon which time the reaction
  4. filtrationThe reaction was filtered through paper
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica using 25–40% EtOAc-hexane

出典と根拠

ORDレコード
ord-74baa1afb8f545a0882bead2dbbf1aa2
出典データセット
uspto-grants-2007_08
特許番号
US07259182B2

反応ノート

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