Methyl 2-(furan-2-yl)-2-oxoacetate → Methyl α-(hydroxyimino)-2-furanacetate
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
Product 1
Reagents, catalysts & solvents 1
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+).