Ammonium Hydroxide → Ethyl 2-furanpropionate

HRID 2166705Notes

Reaction equation

HRID 2166705 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[OH-].[NH4+].[H][H]>[Ni].C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 95368Ethyl 2-furanacrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 61450Ethyl 2-furanpropionateYield 71.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 3-(2-furanyl)acrylate (46.7 g) and conc. ammonium hydroxide solution (25 ml) was hydrogenated in the presence of Raney Nickel (500 mg) at 35° C. until a theoretical amount of hydrogen was taken up. The Raney Nickel was removed by filtering through diatomaceous earth and the filtrate was evaporated at reduced pressure to yield a brown oil. The oil was dissolved in ethyl acetate, washed with distilled water, dried (MgSO4) and the solvent evaporated at reduced pressure to yield ethyl 3-(2-furanyl)-propionate (33.77 g) as a brown oil.

Workup

  1. customThe Raney Nickel was removed
  2. filtrationby filtering through diatomaceous earth
  3. customthe filtrate was evaporated at reduced pressure
  4. customto yield a brown oil
  5. washwashed with distilled water
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated at reduced pressure

Sources & evidence

ORD record
ord-f39271c443a84feaa947dab782609abe
Source dataset
uspto-grants-1983_06
Patent number
US04388317

Reaction notes

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