Aluminium lithium hydride → 2-(2,3-dihydro-1H-indol-1-yl)ethan-1-ol

HRID 55475Notes

Reaction equation

HRID 55475 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)[CH2:3][CH2:2]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)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22199910Methyl (2,3-dihydro-1H-indol-1-yl)acetate

Product 1

HCID 232983052-(2,3-dihydro-1H-indol-1-yl)ethan-1-olYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Preparation 2 was repeated, except that 780 mg of methyl indolin1-ylacetate (prepared as described in Preparation 8), 200 mg of lithium aluminum hydride and 12 ml of anhydrous tetrahydrofuran were used, to give 580 mg of the title compound having Rf=0.31 (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-22a51bca3b2f4b4fbce4d57f55cb9f4b
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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