Methyl 2-furoate → Methyl tetrahydrofuran-2-carboxylate

HRID 1905670Notes

Reaction equation

HRID 1905670 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7]>CO.[Pd]>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 11902Methyl 2-furoate2×

Product 1

HCID 169922Methyl tetrahydrofuran-2-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl furoate (75 g, 0.595 mole) was dissolved in MeOH (150 ml), and poured into a Parr bottle. Air was replaced with argon, and then 10% Pd/C (2.5 g) was added. The atmosphere was replaced with H2 and methyl furoate was hydrogenated at 40 psi for 48 hours. The reaction was filtered through celite pad, and the pad was washed with ether. The filtrate and the wash were combined and distilled to give the title compound (71 g, 0.546 mole, 59° C./5.1 mmHg, 92%) as a colorless liquid.

Workup

  1. additionpoured into a Parr bottle
  2. filtrationThe reaction was filtered through celite pad
  3. washthe pad was washed with ether
  4. distillationdistilled

Sources & evidence

ORD record
ord-16869c8a03114f9583ad4c2e0b766376
Source dataset
uspto-grants-1987_03
Patent number
US04647573

Reaction notes

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