6-Benzyloxy-benzofuran-2-carboxylic acid tert-butyl ester → 6-Hydroxy-benzofuran-2-carboxylic acid tert-butyl ester

HRID 250276Notes

Reaction equation

HRID 250276 reaction equation
[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:16]=[C:15]([O:17]CC3C=CC=CC=3)[CH:14]=[CH:13][C:11]=2[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C1COCC1.CO.[Pd]>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:11]=2[CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 672718976-Benzyloxy-benzofuran-2-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 672716866-Hydroxy-benzofuran-2-carboxylic acid tert-butyl esterYield 97.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-benzyloxy-benzofuran-2-carboxylic acid tert-butyl ester (5.68 g, 17.5 mmol) in THF (50 mL) and MeOH (20 mL) is added to Pd/C (5%, 200 mg). The mixture is stirred under a balloon of hydrogen for 16 hours at room temperature. The mixture is filtered through a pad of diatomaceous earth and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel chromatography eluting with 25% EtOAc/Hexanes to provide the title compound (3.99 g, 97%). LC-ES/MS m/e 233.0 (M−1).

Workup

  1. filtrationThe mixture is filtered through a pad of diatomaceous earth
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is purified by silica gel chromatography
  4. washeluting with 25% EtOAc/Hexanes

Sources & evidence

ORD record
ord-6a57cba0021047d5ba61e62e912909a8
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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