Sodium Sulfate → Benzofuran

HRID 733826Notes

Reaction equation

HRID 733826 reaction equation
COC([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([N+]([O-])=O)=[CH:10][C:8]=2[CH:9]=1)=O.[O-]S([O-])(=O)=O.[Na+].[Na+]>CO.[Pd]>[O:6]1[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=[CH:5]1

Participants

5

Reactant 2

HCID 24436Sodium SulfateHCID 12148807Methyl 5-nitrobenzofuran-2-carboxylate

Product 1

HCID 9223Benzofuran

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2-methoxycarbonyl-5-nitrobenzofuran (2.0 g), 10% Pd/C (2.0 g), Na2SO4 (2.0 g) in MeOH (500 mL) was hydrogenated at 55 PSI for 3 days. The resulting solution was filtered through a pad of celite, concentrated and chromatographed using n-hexanes then 10%, 20% EtOAc/n-hexanes to give (±)-5-amino-2,3-dihydro-2-methoxycarbonyl)benzofuran. 1H NMR (CDCl3): δ 6.69 (d, 1H , J=8.1 Hz), 6.56 (d, 1H, J=1.2 Hz), 6.48 (dd, 1H, J=1.8 and 7.5 Hz), 5.14 (dd, 1H, J=6.6 and 7.2 Hz), 3.79 (s, 3H), 3.47 (dd, 1H, J=10.5 and 10.8 Hz), 3.26 (dd, 1H, J=7.2 and 6.6 Hz); LCMS: purity: 100%; MS (m/e): 194 (MH+).

Workup

  1. filtrationThe resulting solution was filtered through a pad of celite,
  2. concentrationconcentrated
  3. customchromatographed

Sources & evidence

ORD record
ord-7fe8516720884bf08bc9bc6b7959aaad
Source dataset
uspto-grants-2009_09
Patent number
US07589200B2

Reaction notes

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