HCID 18945434, compound → HCID 18945346, compound

HRID 399832Notes

Reaction equation

HRID 399832 reaction equation
C([O:8][C:9]([CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[N:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1)=[O:10])C1C=CC=CC=1>[Pd].CO.O1CCCC1>[C:9]([CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[N:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1)([OH:10])=[O:8]

Participants

5

Reactant 1

HCID 18945434HCID 18945434, compound

Product 1

HCID 18945346HCID 18945346, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium on carbon (0.5 g) was added to a solution of methyl 4-benzyloxycarbonylmethoxy3-(pyrrol-1-yl)benzoate (5.0 g) in methanol (50 ml) and tetrahydrofuran (20 ml) and the mixture was subjected to catalytic reduction at ambient temperature under atmospheric pressure. The catalyst was removed by filtration and filtrate was evaporated in vacuo. To the residue was added a mixture of ethyl acetate and water, and the mixture was adjusted to pH 8 with potassium carbonate. The separated aqueous layer was adjusted to pH 2 with 6N-hydrochloric acid and the mixture was extracted with ethyl acetate. The extract layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give methyl 4-carboxymethoxy3-(pyrrol-1-yl)benzoate (2.26 g).

Workup

  1. customwas subjected to catalytic reduction at ambient temperature under atmospheric pressure
  2. customThe catalyst was removed by filtration and filtrate
  3. customwas evaporated in vacuo
  4. additionTo the residue was added
  5. additiona mixture of ethyl acetate and water
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract layer was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-3ca3e382e0e44c8f82cb3c52d2f12c47
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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