Sodium Hydroxide → HCID 86631686, compound

HRID 2194700Notes

Reaction equation

HRID 2194700 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=2)=[CH:11][C:10]([C:21](OCC)=[O:22])=[N:9]1.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=2)=[CH:11][C:10]([CH:21]=[O:22])=[N:9]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 68410761HCID 68410761, compound

Product 1

HCID 86631686HCID 86631686, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-(2-chlorophenyl)-5-[(6-methylpyridin-2-yl)thio]-1H-pyrazole-3-carboxylate (640 mg) in tetrahydrofuran (10 mL) was added a 1.5 mol/L solution (4.6 mL) of diisobutylaluminum hydride in toluene at −78° C. and the mixture was stirred at the same temperature for 30 min. 1 mol/L Aqueous sodium hydroxide solution was added to the reaction mixture, insoluble materials were filtered off, and the filtrate was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To a solution of the residue in toluene (7 mL) was added manganese dioxide (968 mg) and the mixture was stirred at 80° C. for 1 hr. The reaction mixture was cooled to room temperature and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1) to give the title compound as a yellow oil (yield 420 mg, yield 74%).

Workup

  1. filtrationwere filtered off
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo a solution of the residue in toluene (7 mL) was added manganese dioxide (968 mg)
  7. stirringthe mixture was stirred at 80° C. for 1 hr
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1)

Sources & evidence

ORD record
ord-24dedf30d6294d349c17f7ea25657812
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

Loading…