Tetrahydrofuran → HCID 178503597, compound

HRID 628542Notes

Reaction equation

HRID 628542 reaction equation
Cl[C:2]1[N:6](C)[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]([CH3:17])[CH3:16])=[C:10]([CH3:18])[CH:9]=2)[C:3]=1[CH:19]=[O:20].O1CCCC1.[CH3:26][S-:27].[Na+]>O>[CH:19]([C:3]1[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]([CH3:17])[CH3:16])=[C:10]([CH3:18])[CH:9]=2)=[N:5][NH:6][C:2]=1[S:27][CH3:26])=[O:20]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4378561Sodium methanethiolateHCID 118001333HCID 118001333, compound

Product 1

HCID 178503597HCID 178503597, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature, to a mixture of 5-chloro-4-formyl-3-(4-isopropoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole (described in Reference Preparation example 96) 10 g and tetrahydrofuran 100 ml was added sodium thiomethoxide 2.9 g and the resulting mixture was stirred for eight hours. To the reaction mixture was added water 50 mL and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and was dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 4-formyl-3-(4-isopropoxy-3-methyl-phenyl)-5-methylthio-1H-pyrazole 10.4 g.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-624def0aa5e24af98dda894305079b14
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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