Ethyl 6-chloroindole-2-carboxylate → (6-Chloro-1H-indol-2-yl)methanol

HRID 1008616Notes

Reaction equation

HRID 1008616 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([Cl:15])[CH:9]=2)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:15][C:10]1[CH:9]=[C:8]2[C:13]([CH:14]=[C:6]([CH2:4][OH:3])[NH:7]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7015027Ethyl 6-chloroindole-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 16115151(6-Chloro-1H-indol-2-yl)methanolYield 111.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-chloro-1H-indole-2-carboxylic acid ethyl ester (8.57 g) in THF at 0° C. was added lithium aluminum hydride solution (1M, in THF) dropwise and the reaction mixture was stirred for 3.5 h. The mixture was quenched with H2O, 15% NaOH, and H2O before it was filtered and rinsed with THF. Evaporation of the solvent gave 7.77 g of the crude (6-Chloro-1H-indol-2-yl)-methanol which was used directly in the next step.

Workup

  1. customThe mixture was quenched with H2O, 15% NaOH, and H2O before it
  2. filtrationwas filtered
  3. washrinsed with THF
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d5eb9771409a411c8929968cdb7f8a6d
Source dataset
uspto-grants-2004_09
Patent number
US06797708B2

Reaction notes

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