Methanol → HCID 86747526, compound

HRID 260975Notes

Reaction equation

HRID 260975 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([C:11]2[C:15]([Cl:16])=[C:14]([C:17]([F:20])([F:19])[F:18])[N:13]([CH3:21])[N:12]=2)=[CH:6][C:3]=1C=O.[CH3:22][O:23][C:24](=[O:45])[CH:25]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:46]O>C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([C:11]2[C:15]([Cl:16])=[C:14]([C:17]([F:19])([F:20])[F:18])[N:13]([CH3:21])[N:12]=2)=[CH:6][C:3]=1[CH:46]=[CH:25][C:24]([O:23][CH3:22])=[O:45]

Participants

5

Reactant 3

HCID 887MethanolHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 120071322-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzaldehyde

Product 1

HCID 86747526HCID 86747526, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.3 g (6.8 mmole) 2-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzaldehyde in 25 mL methanol was added 2.27 g (6.8 mmole) methyl(triphenylphosphoranylidene)-acetate, keeping the temperature below 35° C. The reaction mixture was allowed to stir for 15 minutes and diluted with ethyl acetate, washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified chromatographically using 20% ethyl acetate in hexane as the eluent to give 2.0 g (74%) of 3-(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluorophenyl)propenoic acid, methyl ester as a white solid; mp 117° C.

Workup

  1. customthe temperature below 35° C
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified chromatographically

Sources & evidence

ORD record
ord-228ffb07f702445aa67734572e5e3bd7
Source dataset
uspto-grants-1996_06
Patent number
US05530126

Reaction notes

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