ethyl 3,4-dichlorophenylglyoxylate → HCID 87416765, compound

HRID 600970Notes

Reaction equation

HRID 600970 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)=O)[CH3:2].[CH:16]1([O:21][NH2:22])[CH2:20][CH2:19][CH2:18][CH2:17]1>C(O)C>[CH2:1]([O:3][C:4](=[O:15])/[C:5](=[N:22]/[O:21][CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)/[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2736412ethyl 3,4-dichlorophenylglyoxylateHCID 14326481O-Cyclopentylhydroxylamine

Product 1

HCID 87416765HCID 87416765, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

(3,4-Dichloro-phenyl)-oxo-acetic acid ethyl ester (1.08 g, 4.37 mmol) was stirred in ethanol (9.7 mL) and warmed in a 70° C. oil bath. O-Cyclopentyl-hydroxylamine (prepared as in Example 1, 722 mg, 5.25 mmol) was added. After 2 h, the reaction mixture was allowed to cool and concentrated in vacuo. Purification by flash column chromatography (Merck silica gel 60, 40-63 μm; 33% methylene chloride/hexanes) afforded (E)-cyclopentyloxyimino-(3,4-dichloro-phenyl)-acetic acid ethyl ester (371 mg, 26%) as a clear, colorless oil: H1-NMR (400 MHz, CDCl3) δ=1.37 (3H, t, J=7.1 Hz), 1.63 (4H, m), 1.85 (4H, m), 4.36 (2H, q, J=7.1 Hz), 4.94 (1H, m), 7.26 (1H, dd, J=8.3 Hz, J=1.9 Hz), 7.46 (1H, d, J=8.3 Hz), 7.54 (1H, d, J=1.9 Hz).

Workup

  1. temperatureto cool
  2. concentrationconcentrated in vacuo
  3. customPurification by flash column chromatography (Merck silica gel 60, 40-63 μm; 33% methylene chloride/hexanes)

Sources & evidence

ORD record
ord-40018d7cbc91431194d7ce5fcf4e4879
Source dataset
uspto-grants-2011_03
Patent number
US07902248B2

Reaction notes

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