Tetrahydrofuran → Methyl 7-hydroxy-1-methyl-2-indolecarboxylate

HRID 564986Notes

Reaction equation

HRID 564986 reaction equation
O1CCCC1.C([O:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[N:21]([CH3:23])[C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:19]2)C1C=CC=CC=1>[Pd].CO>[OH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[N:21]([CH3:23])[C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:19]2

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 15550275Methyl 7-benzyloxy-1-methyl-2-indolecarboxylate

Product 1

HCID 21194122Methyl 7-hydroxy-1-methyl-2-indolecarboxylateYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a solvent mixture of 50 ml of tetrahydrofuran and 50 ml of methanol was dissolved 2.31 g (7.82 mmol) of methyl 7-benzyloxy-1-methyl-2-indolecarboxylate. After 0.5 g of 10% palladium/carbon was added to the solution, catalytic hydrogenation was performed at ambient temperature under normal pressure. After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 1.63 g (>99%) of methyl 7-hydroxy-1-methyl-2-indolecarboxylate.

Workup

  1. customwas performed at ambient temperature under normal pressure
  2. customAfter completion of the reaction
  3. filtrationthe catalyst was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2f2622b0172d45dd88e3b69670965b30
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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