Ethyl 2-{imidazo[1,2-a]pyridin-2-yl}acetate → 2-(Imidazo[1,2-a]pyridin-2-yl)ethanol

HRID 1953685Notes

Reaction equation

HRID 1953685 reaction equation
[N:1]1[C:2]([CH2:10][C:11](OCC)=[O:12])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:12][CH2:11][CH2:10][C:2]1[N:1]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 10822054Ethyl 2-{imidazo[1,2-a]pyridin-2-yl}acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 104872012-(Imidazo[1,2-a]pyridin-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Preparation 2 was repeated, except that 2. 65 g of ethyl imidazo-[1,2-a]pyridin-2-ylacetate (prepared as described in Preparation 25), 0.5 g of lithium aluminum hydride and 100 ml of tetrahydrofuran were used, to give the title compound as a crude product. This crude product was purified by column chromatography through silica gel, using a gradient elution method, with mixtures of ethyl acetate and ethanol in ratios ranging from 20:1 to 4:1 by volume as the eluent, to give 1.32 g of the title compound, melting at 120.3-126.9° C.

Workup

  1. customA procedure similar to that described in Preparation 2

Sources & evidence

ORD record
ord-82fa56d739f74c3e9c76de57c1cf9f99
Source dataset
uspto-grants-2000_09
Patent number
US06117893

Reaction notes

Loading…