Water → HCID 53836472, compound

HRID 1905402Notes

Reaction equation

HRID 1905402 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([CH3:13])[C:8]=2[CH:14]=[N:15][OH:16])=[CH:4][CH:3]=1.[OH-].[K+].Cl[CH2:22][C:23]1[CH:40]=[CH:39][C:26]([C:27]([O:29][CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:28])=[CH:25][CH:24]=1.O>CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([CH3:13])[C:8]=2[CH:14]=[N:15][O:16][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([O:29][CH2:30][CH2:31][O:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:28])=[CH:39][CH:40]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 20035446HCID 20035446, compoundHCID 57016257HCID 57016257, compound

Product 1

HCID 53836472HCID 53836472, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
30 °C

Procedure

2.0 Grams (0.008 mole) of 5-(4-fluorophenoxy)-1,3-dimethylpyrazole-4-carbaldehyde oxime was dissolved in 20 ml of dimethyl sulfoxide, and after adding 0.65 g (0.0116 mole) of powdery potassium hydroxide, the resulting solution was stirred at 30° C. for 30 minutes. To this solution was added 2.5 g (0.00865 mole) of 2-phenoxyethyl 4-chloromethylbenzoate, and reaction was carried out at from 50° to 60° C. for 1 hour. After completion of the reaction, water was added to the reaction solution which was then extracted with ethyl acetate. The ethyl acetate extract was washed with water and dried, and ethyl acetate was removed by evaporation to obtain an oily product. This oily product was column-chromatographed on silica gel to obtain 3.0 g of the desired compound.

Workup

  1. additionTo this solution was added
  2. waitwas carried out at from 50° to 60° C. for 1 hour
  3. additionwas added to the reaction solution which
  4. extractionwas then extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. customdried
  8. customethyl acetate was removed by evaporation
  9. customto obtain an oily product
  10. customThis oily product was column-chromatographed on silica gel

Sources & evidence

ORD record
ord-96575d9bebd442c0bf96a907e80df7c6
Source dataset
uspto-grants-1989_06
Patent number
US04843068

Reaction notes

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