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

HRID 252854

Reaction equation

HRID 252854 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 266 (1.2 g, 4.26 mmol) in methanol (20 mL) was added 10% 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 through a celite pad, the filtrate was evaporated under reduced pressure, and the resulting solid dried under vacuum to afford 267 as a white solid (700 mg, 86%). 1H NMR: (DMSO) δ 10.07 (s, 1H), 7.63 (s, 1H), 7.56 (d, J=8.0 Hz, 1H), 6.98 (s, 1H), 6.84 (d, J=9.0 Hz, 1H), 3.84 (s, 3H).

Workup

  1. customThe flask was purged with hydrogen gas for 1 minute
  2. filtrationThe palladium was filtered through a celite pad
  3. customthe filtrate was evaporated under reduced pressure
  4. customthe resulting solid dried under vacuum

Sources & evidence

ORD record
ord-9d7cd4e7e2ba4400afe2356d62f39d9c
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Linked notes

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