Methyl 2-furoate → Methyl tetrahydrofuran-2-carboxylate

HRID 980852Notes

Reaction equation

HRID 980852 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-68792c853ad54b878419c2712f6cb21a
Source dataset
uspto-grants-1987_01
Patent number
US04639461

Reaction notes

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