Methyl indole-7-carboxylate → (1H-indol-7-yl)methanol

HRID 1198533Notes

Reaction equation

HRID 1198533 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[C:16](OC)=[O:17])[CH:9]=[CH:8]1>O1CCCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH2:16][OH:17])[CH:9]=[CH:8]1

Participants

4

Reactant 2

HCID 676694Methyl indole-7-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2773460(1H-indol-7-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Solid lithium aluminum hydride (1.0 g) was added in portions over 1 hour to a stirred solution of methyl 7-indolecarboxylate (6.7 g) in tetrahydrofuran (100 ml). The mixture was stirred for a further 2 hours then excess lithium aluminium hydride was destroyed by addition of acetic acid, the mixture was diluted with aqueous sodium hydroxide and extracted with ethyl acetate. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:9 to 1:2) to give the product.

Workup

  1. customexcess lithium aluminium hydride was destroyed by addition of acetic acid
  2. additionthe mixture was diluted with aqueous sodium hydroxide
  3. extractionextracted with ethyl acetate
  4. customThe extract was dried
  5. customevaporated
  6. customthe residue was chromatographed on silica in ethyl acetate-hexane (1:9 to 1:2)
  7. customto give the product

Sources & evidence

ORD record
ord-ab96b6071c004d449d48248a61662c00
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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