Water → 6-(Benzyloxy)-5-methoxy-1H-indole-2-carbaldehyde

HRID 11121Notes

Reaction equation

HRID 11121 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[C:9]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:8]=2)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.[O-2].[O-2].[Mn+4]>[CH2:17]([O:16][C:9]1[CH:8]=[C:7]2[C:12]([CH:13]=[C:5]([CH:3]=[O:2])[NH:6]2)=[CH:11][C:10]=1[O:14][CH3:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21980369Methyl 6-(benzyloxy)-5-methoxy-1H-indole-2-carboxylate

Product 1

HCID 219808376-(Benzyloxy)-5-methoxy-1H-indole-2-carbaldehydeYield 82%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ester (56) (1.0 g, 3.22 mmol) prepared as described in example 248 in tetrabydrofuran (10 mL) was added a suspension of lithium aluminum hydride (0.150 g, 3.86 mmol) in tetrahydrofuran (10 mL) dropwise, the reaction mixture was stirred at room temperature for 20 min. Water (1 mL) was added dropwise and then dilute sodium hydroxide (1 mL) was added, the solution was stirred for 10 min and then filtered through Celite and concentrated. The resulting yellow oil was dissolved in chloroform (20 mL) and then manganese dioxide (2.2 g, 26.0 mmol) was added, the reaction mixture was heated at 50° C. for 1 h and then filtered through Celite and concentrated. The residue was recrystallized from dichloromethane to give 6-(benzyloxy)-5-methoxy-1H-indole-2-carbaldehyde (57) (0.74 g, 82%) as pale yellow needles. Found: C, 72.53; H, 5.42; N, 4.92. C17H15NO3 requires: C, 72.58; H, 5.37; N, 4.98.

Workup

  1. additionwas added
  2. stirringthe solution was stirred for 10 min
  3. filtrationfiltered through Celite
  4. concentrationconcentrated
  5. dissolutionThe resulting yellow oil was dissolved in chloroform (20 mL)
  6. temperaturethe reaction mixture was heated at 50° C. for 1 h
  7. filtrationfiltered through Celite
  8. concentrationconcentrated
  9. customThe residue was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-2762c7091e4841c693b05eddf337a72e
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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