Water → HCID 22926802, compound

HRID 1985423Notes

Reaction equation

HRID 1985423 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:20](OC)=[O:21])[C:14]=2[CH:13]=[CH:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=[O:21])[C:14]=2[CH:13]=[CH:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22926878HCID 22926878, compound

Product 1

HCID 22926802HCID 22926802, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3.6 g of Methyl 1-(2-benzyloxyethyl)-1H-indol-4-carboxylate was dissolved in 40 ml of diethyl ether, and 0.44 g of lithium aluminum hydride was added under ice-cooling. After stirring at room temperature for 10 minutes, the reaction solution was cooled with ice, and diethyl ether and water were added. When the insoluble substances adhered to and solidified on the wall of the flask, the reaction solution was dried over anhydrous magnesium sulfate, then the solvent was evaporated. The residue was dissolved in 40 ml of dichloromethane, 20 g of manganese dioxide was added, and the mixture was stirred at room temperature for 2 hours. After filtering off the manganese dioxide through Celite, and washing through with ethyl acetate, the solvent was evaporated, to give 1.5 g of the title compound.

Workup

  1. temperaturecooling
  2. additionwere added
  3. dry with materialthe reaction solution was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. dissolutionThe residue was dissolved in 40 ml of dichloromethane
  6. addition20 g of manganese dioxide was added
  7. stirringthe mixture was stirred at room temperature for 2 hours
  8. filtrationAfter filtering off the manganese dioxide through Celite
  9. washwashing through with ethyl acetate
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-eaaa04f0e53041d690a367b783acceb6
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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