Methyl (furan-2-yl)(oxo)acetate → Methyl α-(hydroxyimino)-2-furanacetate

HRID 1003964Notes

Reaction equation

HRID 1003964 reaction equation
Cl.[NH2:2][OH:3].O=[C:5]([C:10]1[O:11][CH:12]=[CH:13][CH:14]=1)[C:6]([O:8][CH3:9])=[O:7]>CO>[OH:3][N:2]=[C:5]([C:10]1[O:11][CH:12]=[CH:13][CH:14]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 118422Methyl (furan-2-yl)(oxo)acetateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 73472306Methyl α-(hydroxyimino)-2-furanacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxylamine hydrochloride (0.951 g) was added to a stirred solution of methyl 2-oxo-2-(2-furanyl)acetate (2.107 g) in methanol (30 ml). The mixture was stirred for 3 h, then the solvent was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over magnesium sulphate and evaporated. The title oxime was isolated by column chromatography of the residue using gradient elution (Kieselgel:3:1 to 1:1 hexane:ethyl acetate). (Found: M+, 169.0378. C7H7NO4 requires M, 169.0375). νmax (CHCl3 /cm-1 3555, 3278 and 1739. δH (250 MHz, CDCl3), 3.95 (3H, s), 6.57 (1H, dd, J 1.58 and 3.48), 7.45 (1H, d, J 3.22), 7.58 (1H, d, J 2.11), 9.75 (1H, br.s), m/z (EI) 169 (M+).

Workup

  1. customthe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-34a81fac435b4a11838f2f1b8e76bf25
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Reaction notes

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