5-Methoxyindoleacetic acid → 5-Methoxytryptophol

HRID 1941113Notes

Reaction equation

HRID 1941113 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13](O)=[O:14].[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][OH:14]

Participants

6

Reactant 3

HCID 189865-Methoxyindoleacetic acidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydride

Product 1

HCID 128355-Methoxytryptophol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15 g of (5-methoxyindol-3-yl)acetic acid (0.073 mol) in 100 ml of tetrahydrofuran is added to a suspension of 2.1 g (0.219 mol) of lithium aluminum hydride in 100 ml of ethyl ether and the reaction mixture is brought to reflux for 6 hours. The reaction mixture is then hydrolyzed with 80 ml of a saturated aqueous magnesium sulfate solution. The whole mixture is filtered through celite and the solvents are evaporated under vacuum. The residue is taken up in a small amount of water and extracted a number of times with dichloromethane. The product is obtained after evaporation of the solvant.

Workup

  1. temperatureto reflux for 6 hours
  2. filtrationThe whole mixture is filtered through celite
  3. customthe solvents are evaporated under vacuum
  4. extractionextracted a number of times with dichloromethane
  5. customThe product is obtained
  6. customafter evaporation of the solvant

Sources & evidence

ORD record
ord-f4f4bc72d657402f9b183974ae18efa9
Source dataset
uspto-grants-1997_12
Patent number
US05703070

Reaction notes

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