Sodium Hydroxide → HCID 86631688, compound

HRID 2194701Notes

Reaction equation

HRID 2194701 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]([O:20][CH3:21])[N:15]=2)=[CH:11][C:10]([C:22](OCC)=[O:23])=[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]([O:20][CH3:21])[N:15]=2)=[CH:11][C:10]([CH:22]=[O:23])=[N:9]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 68411241HCID 68411241, compound

Product 1

HCID 86631688HCID 86631688, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of ethyl 1-(2-chlorophenyl)-5-[(6-methoxypyridin-2-yl)thio]-1H-pyrazole-3-carboxylate (594 mg) in tetrahydrofuran (6 mL) was added a solution (3 mL) of 1.5 mol/L diisobutylaluminum hydride in toluene at −78° C., and the mixture was stirred at the same temperature for 30 min and at −30° C. for 1 hr. 1 mol/L Aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture 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 (8 mL) was added manganese dioxide (1.79 g) 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=4:1) to give the title compound as a yellow oil (yield 406 mg, yield 77%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo a solution of the residue in toluene (8 mL) was added manganese dioxide (1.79 g)
  6. stirringthe mixture was stirred at 80° C. for 1 hr
  7. temperatureThe reaction mixture was cooled to room temperature
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1)

Sources & evidence

ORD record
ord-b1194f7090e64b0ea205922f5b4f5574
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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