methyl 2-(1H-indol-1-yl)acetate → 1H-Indole-1-ethanol

HRID 55476Notes

Reaction equation

HRID 55476 reaction equation
[N:1]1([CH2:10][C:11](OC)=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[N:1]1([CH2:10][CH2:11][OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 966836methyl 2-(1H-indol-1-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 137349961H-Indole-1-ethanolYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Preparation 2 was repeated, except that 6.20 g of methyl indol-1-ylacetate (prepared as described in Preparation 12), 1.50 g of lithium aluminum hydride and 220 ml of anhydrous tetrahydrofuran were used, to give 5.25 g of the title compound having Rf=0.33 (on silica gel thin layer chromatography using a 2:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 2

Sources & evidence

ORD record
ord-20248c6a1b064c0fb2d56bc3d1e74761
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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