(5,7-Difluoro-6-hydroxy-benzofuran-3-yl)-acetic acid methyl ester → (5,7-Difluoro-6-hydroxy-2,3-dihydro-benzofuran-3-yl)-acetic acid methyl ester

HRID 62896Notes

Reaction equation

HRID 62896 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[C:9]2[CH:10]=[C:11]([F:16])[C:12]([OH:15])=[C:13]([F:14])[C:8]=2[O:7][CH:6]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH:5]1[C:9]2[CH:10]=[C:11]([F:16])[C:12]([OH:15])=[C:13]([F:14])[C:8]=2[O:7][CH2:6]1

Participants

4

Reactant 1

HCID 90118454(5,7-Difluoro-6-hydroxy-benzofuran-3-yl)-acetic acid methyl ester

Product 1

HCID 90118284(5,7-Difluoro-6-hydroxy-2,3-dihydro-benzofuran-3-yl)-acetic acid methyl esterYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(5,7-Difluoro-6-hydroxy-benzofuran-3-yl)-acetic acid methyl ester (0.16 g, 0.66 mmol) obtained in Step C of Preparation Example 50 was dissolved in MeOH, and 10% Pd/C (30 mg) was added thereto. The mixture was stirred at room temperature under hydrogen atmosphere for 3 hours and then filtered. The filtrate was distilled under reduced pressure and then purified using EtOAc/Hex (1:4) solution by column chromatography to obtain the title compound (0.13 g, 81%).

Workup

  1. filtrationfiltered
  2. distillationThe filtrate was distilled under reduced pressure
  3. custompurified

Sources & evidence

ORD record
ord-e20739668de446ff8489774ec68ed6d4
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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