Ammonium Chloride → HCID 15631684, compound

HRID 1721941Notes

Reaction equation

HRID 1721941 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]([C:11]2[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=2)=O)[CH:5]=[CH:4][C:3]=1[OH:17].[CH2:18]([Li])CCC.[Cl-].[NH4+]>O1CCCC1.CS(C)=O.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCCCCC>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]([C:11]2[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=2)=[CH2:18])[CH:5]=[CH:4][C:3]=1[OH:17]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 15631674HCID 15631674, compoundHCID 178418339Butyllithium

Product 1

HCID 15631684HCID 15631684, compound

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8058HexaneSolventHCID 21830753dimethylsulfoxide THFSolvent

Procedure

A solution of 2.71 g of 2,3-dichloro-4-(1-methyl-5-pyrazolylcarbonyl)phenol in tetrahydrofuran-dimethylsulfoxide is added dropwise to an ylide solution prepared from a solution of 8.57 g of methyltriphenylphophonium bromide in tetrahydrofurandimethylsulfoxide and 13.8 ml of 1.6M n-butyl lithium in hexane. The mixture is stirred at room temperature for 18 hours, and further stirred at 65° C. for 2 hours. The reaction mixture is poured into an aqueous saturated ammonium chloride solution and then extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography to give 2.41 g of 2,3-dichloro-4-[1-(1-methyl-5-pyrazolyl)vinyl]phenol.

Workup

  1. stirringfurther stirred at 65° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a95995ff4e8a4cf0a6062b6f38156f44
Source dataset
uspto-grants-1989_08
Patent number
US04853404

Reaction notes

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