Sodium borohydride → (1-Methyl-1H-indol-7-yl)methanol

HRID 2360479Notes

Reaction equation

HRID 2360479 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH:11]=[O:12])[CH:4]=[CH:3]1.[BH4-].[Na+]>C(O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][OH:12])[CH:4]=[CH:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 110409791-methyl-1H-indole-7-carbaldehyde

Product 1

HCID 24229741(1-Methyl-1H-indol-7-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.8 g 1-methyl-1H-indole-7-carbaldehyde are dissolved in 150 ml of ethanol, cooled to 0° C. and combined batchwise with 1.3 g sodium borohydride. After the addition has ended the cooling bath is removed and the mixture is stirred for another 2 hours at ambient temperature. Then 68 ml 1 M sodium hydroxide solution are added, the mixture is stirred for 10 minutes and then most of the ethanol is eliminated in vacuo. The residue is divided between water and ethyl acetate and the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed with saturated aqueous sodium chloride solution and dried on magnesium sulphate. Then the solvents are eliminated in vacuo and the residue is dried in vacuo.

Workup

  1. additionAfter the addition
  2. customis removed
  3. additionThen 68 ml 1 M sodium hydroxide solution are added
  4. stirringthe mixture is stirred for 10 minutes
  5. extractionthe aqueous phase is extracted twice with ethyl acetate
  6. washThe combined organic phases are washed with saturated aqueous sodium chloride solution
  7. customdried on magnesium sulphate
  8. customthe residue is dried in vacuo

Sources & evidence

ORD record
ord-7aee1d76392644c39351d279d92738f0
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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