Methyl 5-ethenylfuran-2-carboxylate → Methyl 5-ethylfuran-2-carboxylate

HRID 1961173Notes

Reaction equation

HRID 1961173 reaction equation
[CH:1]([C:3]1[O:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1)=[CH2:2]>CO>[CH2:1]([C:3]1[O:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1)[CH3:2]

Participants

3

Reactant 1

HCID 57826801Methyl 5-ethenylfuran-2-carboxylate

Product 1

HCID 13637632Methyl 5-ethylfuran-2-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-ethenyl-2-furancarboxylate (1.3 g, 8.54 mmol) in methanol (15 ml) was added PdOH2 (0.240 g, 1.71 mmol). The reaction mixture was hydrogenated at 1 atm (balloon) for 1 h. The solution was then purged with N2, filtered through Celite and concentrated affording methyl 5-ethyl-2-furancarboxylate (1.2 g, 7.16 mmol, 84% yield) as a clear oil which was used without further purification: LCMS (ES) m/e 155 (M+H)+.

Workup

  1. customThe solution was then purged with N2
  2. filtrationfiltered through Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e9e05fba55404295bcae3c8c943419e2
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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