Isoamyl Alcohol → HCID 57117418, compound

HRID 260962Notes

Reaction equation

HRID 260962 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([C:15]2[C:19]([Cl:20])=[C:18]([C:21]([F:24])([F:23])[F:22])[N:17]([CH3:25])[N:16]=2)=[CH:10][C:3]=1[O:4][CH:5]([CH3:9])[C:6]([OH:8])=[O:7].C(Cl)(=O)C(Cl)=O.[CH3:32][CH:33]([CH3:37])[CH2:34][CH2:35]O>C(Cl)Cl.CN(C=O)C.O>[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([C:15]2[C:19]([Cl:20])=[C:18]([C:21]([F:23])([F:24])[F:22])[N:17]([CH3:25])[N:16]=2)=[CH:10][C:3]=1[O:4][CH:5]([CH3:9])[C:6]([O:8][CH2:35][CH2:34][CH:33]([CH3:37])[CH3:32])=[O:7]

Participants

7

Reactant 3

HCID 31260Isoamyl AlcoholHCID 65578Oxalyl chlorideHCID 19436753HCID 19436753, compound

Product 1

HCID 57117418HCID 57117418, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.9 g (5.0 mmole) of 2-(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluorophenoxy)-propanoic acid in 50 mL methylene chloride was added 1.3 mL (15.0 mmole) oxalyl chloride over 5 minutes, causing the evolution of gas. When this evolution ceased, one drop of DMF was added and the solution stirred until the gas evolution ceased. The solution was stripped to dryness in vacuo. The acid chloride was dissolved in 40 mL of 3-methyl-1-butanol and heated to reflux for one hour. The reaction mixture was cooled, diluted with 100 mL cold water and extracted with ethyl acetate. The ethyl acetate was washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified chromatographically using 25% ethyl acetate in hexane as the eluent to give 2.17 g (95%) of 2-(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluorophenoxy)-propanoic acid, 3-methylbutyl ester as a white solid; mp 128° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for one hour
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate was washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified chromatographically

Sources & evidence

ORD record
ord-a2c070b0110a4a3da64f0f03d65a5dbf
Source dataset
uspto-grants-1996_06
Patent number
US05530126

Reaction notes

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