4-Benzyloxy-3-[(E)-2-phenylvinyl]indole → 4-Hydroxy-3-(2-phenylethyl)indole

HRID 230889Notes

Reaction equation

HRID 230889 reaction equation
C([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11](/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:12][NH:13]2)C1C=CC=CC=1>C(O)C.[C].[Pd]>[OH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:12][NH:13]2

Participants

4

Reactant 1

HCID 671363114-Benzyloxy-3-[(E)-2-phenylvinyl]indole

Product 1

HCID 231035714-Hydroxy-3-(2-phenylethyl)indoleYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-benzyloxy-3-[(E)-2-phenylvinyl]indole (0.1 g) in ethanol (5 mL) was added 10% palladium-carbon powder (25 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere overnight. The insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=3/1) to give the title compound (70 mg).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-7d65a8af08834ba38b106643260bb247
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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