Methyl 6-(phenylmethoxy)-2-benzofurancarboxylate → Methyl 6-hydroxy-1-benzofuran-2-carboxylate

HRID 1907761Notes

Reaction equation

HRID 1907761 reaction equation
C([O:8][C:9]1[CH:21]=[CH:20][C:12]2[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[O:15][C:11]=2[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:21]=[CH:20][C:12]2[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[O:15][C:11]=2[CH:10]=1

Participants

4

Reactant 1

HCID 12082973Methyl 6-(phenylmethoxy)-2-benzofurancarboxylate

Product 1

HCID 12082972Methyl 6-hydroxy-1-benzofuran-2-carboxylateYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 393 (1.2 g, 4.26 mmol) in MeOH (20 mL) was added palladium on charcoal (250 mg). The flask was purged with hydrogen gas for 1 minute and then the reaction was stirred under a hydrogen atmosphere for 15 hours. The palladium was filtered off through Celite and the filtrate was evaporated via rotary evaporation, and the resulting solid dried under vacuum to afford 394 as a white solid (700 mg, 86%).

Workup

  1. customThe flask was purged with hydrogen gas for 1 minute
  2. filtrationThe palladium was filtered off through Celite
  3. customthe filtrate was evaporated via rotary evaporation
  4. customthe resulting solid dried under vacuum

Sources & evidence

ORD record
ord-f6affbb560244fcd9ae7ba98f7fc92b0
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

Loading…