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

HRID 854502노트

반응식

HRID 854502 반응식
[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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 23938Palladium촉매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-74baa1afb8f545a0882bead2dbbf1aa2
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259182B2

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