Formic Acid → Methyl 2-amino-2-(furan-2-yl)acetate

HRID 530195Notes

Reaction equation

HRID 530195 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[N:11]OC)[C:7]([O:9][CH3:10])=[O:8].C(O)=O>CO.O.[Zn]>[NH2:11][CH:6]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 2

HCID 284Formic AcidHCID 87797286Methyl 2-(furan-2-yl)-2-(methoxyimino)acetate

Product 1

HCID 3357701Methyl 2-amino-2-(furan-2-yl)acetateYield 68.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a magnetically stirred solution of methyl 2-(furan-2-yl)-2-(methoxyimino)acetate (17.50 g, 96 mmol) in 300 mL of MeOH was added 200 mL of a solution of 50% formic acid in water. The reaction mixture was cooled to 0° C. (ice bath) and zinc dust (18.74 g, 287 mmol) was added. After stirring at room temperature for 18 hr, the reaction mixture was filtered through a plug of Celite and the plug was washed with MeOH. Solvent was removed on the rotary evaporator and the yellow residue was dissolved in 50 mL of water, basified to pH 10 with a saturated solution of Na2CO3 and extracted with 3×100 mL of EtOAc. After drying (MgSO4) the organic extracts, solvent removal gave 10.2 g of methyl 2-amino-2-(furan-2-yl)acetate as an orange liquid.

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered through a plug of Celite
  3. washthe plug was washed with MeOH
  4. customSolvent was removed on the rotary evaporator
  5. dissolutionthe yellow residue was dissolved in 50 mL of water
  6. extractionextracted with 3×100 mL of EtOAc
  7. dry with materialAfter drying (MgSO4)
  8. customthe organic extracts, solvent removal

Sources & evidence

ORD record
ord-7e989eb6ee0f4ca78f7d3dc0c825ef42
Source dataset
uspto-grants-2016_05
Patent number
US09353060B2

Reaction notes

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