Methyl 2-furoate → Methyl tetrahydrofuran-2-carboxylate

HRID 616314Notes

Reaction equation

HRID 616314 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[H][H]>[Pd].CO>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 11902Methyl 2-furoateHCID 178418361HCID 178418361, compound

Product 1

HCID 169922Methyl tetrahydrofuran-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl furoate is dissolved in 180 ml. of methanol. Thereafter 1 g. of 5 percent palladium-on-charcoal is added. This mixture is then hydrogenated at 1 to 3 atmospheres. After 45 hr. 0.79 moles of hydrogen are consumed. The black mixture is then filtered through Celite using 50 ml. of methanol to wash the reaction flask and filter. Evaporation of the filtrate under reduced pressure at 40°-45° C. bath temperature yields 51 g. of a yellow oil which is thereafter distilled, collecting that fraction boiling at 32°-35° C. Thereby, methyl tetrahydrofuroate (46.7 g.) is prepared.

Workup

  1. filtrationThe black mixture is then filtered through Celite
  2. washof methanol to wash the reaction flask
  3. filtrationfilter
  4. customEvaporation of the filtrate under reduced pressure at 40°-45° C. bath temperature
  5. customyields 51 g
  6. distillationof a yellow oil which is thereafter distilled
  7. customcollecting that fraction boiling at 32°-35° C

Sources & evidence

ORD record
ord-d222af5430c8479c86ff4190d42802d6
Source dataset
uspto-grants-1978_02
Patent number
US04073808

Reaction notes

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