Ammonium formate → HCID 66920371, compound

HRID 1367763Notes

Reaction equation

HRID 1367763 reaction equation
[CH2:1]([O:8][CH2:9][C:10](=O)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+:21]>CO>[CH2:1]([O:8][CH2:9][C:10]([NH2:21])=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 9813448Ethyl 4-(benzyloxy)-3-oxobutanoate

Product 1

HCID 66920371HCID 66920371, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 14.48 g (0.6129 mol) of ethyl 4-benzyloxy-3-oxo-butanoate in 145 ml of methanol, 20.54 g (0.3258 mol) of ammonium formate was added, and the resulting mixture was heated under reflux for 16 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and the solvent was evaporated off under reduced pressure. To the reside, 100 ml of ethyl acetate and 100 ml of water were added, and the mixture was stirred at room temperature for 30 minutes. Then, the organic layer was separated and the aqueous layer was extracted with 50 ml of ethyl acetate. The organic layers were combined, washed twice with each 50 ml of a brine and dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue was then distilled to give the objective ethyl 4-benzyloxy-3-amino-2-butenoate (7.61 g, colorless liquid). The yield was 52.8%.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 16 hours
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated off under reduced pressure
  5. additionTo the reside, 100 ml of ethyl acetate and 100 ml of water were added
  6. customThen, the organic layer was separated
  7. extractionthe aqueous layer was extracted with 50 ml of ethyl acetate
  8. washwashed twice with each 50 ml of a brine
  9. dry with materialdried over sodium sulfate
  10. customThe solvent was removed under reduced pressure
  11. distillationthe residue was then distilled

Sources & evidence

ORD record
ord-788da16f00674b81b847006558c80153
Source dataset
uspto-grants-2011_02
Patent number
US07893296B2

Reaction notes

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