Methanol → [5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-pyrazol-3-yl]methanol

HRID 526705Notes

Reaction equation

HRID 526705 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21](O)=[O:22])[C:9]=2[CH3:24])=[CH:4][CH:3]=1.B.CO>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([CH2:21][OH:22])[C:9]=2[CH3:24])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 15194215-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 16086920[5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-pyrazol-3-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5 g of 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid in 130 ml of THF, were added dropwise 40 ml of a 1M solution of borane in THF at room temperature. Then, the reaction mixture was heated to reflux for 10 h. The reaction mixture was cooled to room temperature and 20 ml of methanol were carefully added. The solvents were removed under reduced pressure and the residue was dissolved in ethyl acetate. The organic layer was washed with 1 M hydrochloric acid saturated sodium chloride solution and saturated sodium hydrogen carbonate solution. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The product was obtained as a white solid and was used without further purification. Yield: 4.6 g.

Workup

  1. temperatureThen, the reaction mixture was heated
  2. temperatureto reflux for 10 h
  3. customThe solvents were removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe organic layer was washed with 1 M hydrochloric acid saturated sodium chloride solution and saturated sodium hydrogen carbonate solution
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product was obtained as a white solid
  10. customwas used without further purification

Sources & evidence

ORD record
ord-a554e6bc6f6f4c408d2f6768e30e831c
Source dataset
uspto-grants-2016_05
Patent number
US09346762B2

Reaction notes

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