Ethyl Acetate → HCID 22993710, compound

HRID 1167643Notes

Reaction equation

HRID 1167643 reaction equation
[O:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1.C(OCC)(=O)C.[H][H]>CO.[Rh]>[O:1]1[CH2:5][CH:4]([C:6]([O:8][CH3:9])=[O:7])[CH:3]([C:10]([O:12][CH3:13])=[O:11])[CH2:2]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 303461dimethyl furan-3,4-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 22993710HCID 22993710, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

Dimethyl 3,4-furandicarboxylate (5.20 g, 28.0 mmol) was combined with 5% Rhodium/C in methanol (30 mL) and ethyl acetate (10 mL) in a Parr shaker bottle. The reaction was charged to 50 psi hydrogen and was shaken for 8.5 h. The reaction was filtered over celite, concentrated in vacuo to give the dimethyl 3,4-tetrahydrofuran dicarboxylate (5.2 g, 100%) as an oil MS (M−CH3OH)+=156.

Workup

  1. filtrationThe reaction was filtered over celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aadcb005d49e4a66a8b059231910b2b0
Source dataset
uspto-grants-2003_09
Patent number
US06620823B2

Reaction notes

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