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

HRID 54524Notes

Reaction equation

HRID 54524 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) is 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 aluminum hydride was destroyed by addition of acetic acid, the mixture is diluted with aqueous sodium hydroxide and extracted with ethyl acetate. The extract is dried and evaporated and the residue is chromatographed on silica in ethyl acetate-hexane (1:9 to 1:2) to give the product.

Workup

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

Sources & evidence

ORD record
ord-2da6b86adf064be687ad7b5c0bee226d
Source dataset
uspto-grants-1997_04
Patent number
US05622969

Reaction notes

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