Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate → 2-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-(trifluoromethyl)-3(2H)-pyridazinone

HRID 1018442Notes

Reaction equation

HRID 1018442 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([NH:9][N:10]=[CH:11][C:12](=O)[C:13]([F:16])([F:15])[F:14])=[C:4]([F:18])[CH:3]=1.[C:19]([CH2:24][CH:25]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(OCC)=[O:20]>O1CCCC1>[F:18][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([OH:8])=[CH:6][C:5]=1[N:9]1[C:19](=[O:20])[C:24]([CH3:25])=[C:12]([C:13]([F:16])([F:15])[F:14])[CH:11]=[N:10]1

Participants

4

Reactant 2

HCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoateHCID 691427153,3,3-Trifluoro-2-oxopropanal (4-chloro-2-fluoro-5-hydroxyphenylhydrazone)

Product 1

HCID 99490912-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-(trifluoromethyl)-3(2H)-pyridazinoneYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Then, 12.9 g of 3,3,3-trifluoro-2-oxopropanal 1-(4-chloro-2-fluoro-5-hydroxyphenylhydrazone) and 22.3 g of carbethoxyethylidenetriphenylphosphorane were dissolved in 110 ml of tetrahydrofuran, and the solution was heated under reflux for 3 hours. The solvent was distilled out under reduced pressure, and the residue was subjected to silica gel chromatography, which afforded 8.8 g of 2-(2-fluoro-4-chloro-5-hydroxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one (compound 1-391).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 3 hours
  3. distillationThe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-c26f6f5539df4b919a9e8f28c595b1db
Source dataset
uspto-grants-2002_11
Patent number
US06482773B1

Reaction notes

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