Sodium Acetate → Ethyl 3-fluoro-2-[(1,1-dimethylethoxy)methyl]-alpha-(methoxyimino)-benzeneacetate

HRID 1739656

Reaction equation

[F:1][C:2]1[C:3]([CH2:15][O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:4]([C:8](=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.[O:22]([NH2:24])[CH3:23].C([O-])(=O)C.[Na+]>C(O)C>[F:1][C:2]1[C:3]([CH2:15][O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:4]([C:8](=[N:24][O:22][CH3:23])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 79 g (0.28 mole) of ethyl 3-fluoro-2-[(1,1-dimethylethoxy)methyl]-α-oxo-benzeneacetate in 300 mL of ethyl alcohol was added 100 mL (0.39 mole, 30% aq) of methoxylamine HCl followed by 33 g (0.4 mole) of sodium acetate. The mixture was then heated at 60° C. for three hours. After cooling to room temperature, the salts were filtered and the mixture was concentrated in vacuo. Water and EtOAc were added, the layers separated, and the organics were washed with saturated NaHCO3, brine and dried over MgSO4. After filtration, the solution was concentrated in vacuo to give 86.1 g of ethyl 3-fluoro-2-[(1,1-dimethylethoxy)methyl]-α-(methoxyimino)-benzeneacetate as a lightly tinted oil, 1:2 ratio of oxime isomers by gas chromatography.

Workup

temperatureAfter cooling to room temperature
filtrationthe salts were filtered
concentrationthe mixture was concentrated in vacuo
additionWater and EtOAc were added
customthe layers separated
washthe organics were washed with saturated NaHCO3, brine
dry with materialdried over MgSO4
filtrationAfter filtration
concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record: ord-4dff60d5c90b493f8b75994341426f3e
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05968875

Linked notes

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