Methyl 5-methoxy-1-benzofuran-2-carboxylate → Methyl 5-methoxy-2,3-dihydro-1-benzofuran-2-carboxylate

HRID 2113142Notes

Reaction equation

HRID 2113142 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:8]=2[CH:9]=1)=[O:4]>C(O)C.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8]2[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:7]=2[O:6]1)=[O:4]

Participants

4

Reactant 1

HCID 14916651Methyl 5-methoxy-1-benzofuran-2-carboxylate

Product 1

HCID 11447108Methyl 5-methoxy-2,3-dihydro-1-benzofuran-2-carboxylateYield 62.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Methoxy-benzofuran-2-carboxylic acid methyl ester (2.2 g, 10 mmol) and 10% Pd-C (0.44 g) in ethanol (50 mL) were agitated under hydrogen (45 psi) for 72 hrs. The reaction mixture was filtered and the filtrate was concentrated. The residue was chromatographed on silica gel eluting with 8:2 hexane:ethyl acetate to give 1.3 g 5-methoxy-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was chromatographed on silica gel eluting with 8:2 hexane

Sources & evidence

ORD record
ord-d362fb305a2d4c4a84e1cf84eba3be5b
Source dataset
uspto-grants-2009_04
Patent number
US07524882B2

Reaction notes

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