1-[1-(4-Chlorophenyl)pyrazol-3-yl]oxypropan-2-one → methyl (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-4-methylpent-3-enoate

HRID 918759Notes

Reaction equation

HRID 918759 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15](=O)[CH3:16])=[N:9]2)=[CH:4][CH:3]=1.C(OP([CH2:26]/[C:27](=[N:32]\[O:33][CH3:34])/[C:28]([O:30][CH3:31])=[O:29])(OCC)=O)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][C:10]([O:13][CH2:14]/[C:15](/[CH3:16])=[CH:26]\[C:27](=[N:32]/[O:33][CH3:34])\[C:28]([O:30][CH3:31])=[O:29])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 896505491-[1-(4-Chlorophenyl)pyrazol-3-yl]oxypropan-2-oneHCID 89661752methyl (2Z)-3-diethoxyphosphoryl-2-methoxyiminopropanoate

Product 1

HCID 89661753methyl (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-4-methylpent-3-enoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5.26 g (21.0 mmol) 1-[1-(4-chlorophenyl)pyrazol-3-yl]oxypropan-2-one and 7.20 g (26.9 mmol) methyl (2Z)-3-diethoxyphosphoryl-2-methoxyimino-propanoate (which can be prepared as described for the dimethoxy derivative [(Tetrahedron Let 29, 3361-3364 (1988)] in 100 ml THF have been added at ambient temperature with stirring 2.59 g (23.1 mmol) potassium tert.-butylate. Stirring was continued over night. After removal of the solvent in vacuo the mixture was purified by chromatography on silica with heptane/ethyl acetate. 1.07 g of a 80:20 E:Z-mixture have been collected. This has been used directly for the next step.

Workup

  1. additionhave been added at ambient temperature
  2. waitwas continued over night
  3. customAfter removal of the solvent in vacuo the mixture
  4. customwas purified by chromatography on silica with heptane/ethyl acetate
  5. custom1.07 g of a 80:20 E:Z-mixture have been collected

Sources & evidence

ORD record
ord-d7d27b1ba2f54854a557f6f912d71b09
Source dataset
uspto-grants-2016_03
Patent number
US09271501B2

Reaction notes

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