Trimethylsilane → HCID 117724701, compound

HRID 628540Notes

Reaction equation

HRID 628540 reaction equation
[CH:1]([C:3]1[C:4]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH3:20])[CH3:19])=[C:13]([CH3:21])[CH:12]=2)=[N:5][N:6]([CH3:10])[C:7]=1[O:8][CH3:9])=O.C[SiH](C)C>FC(F)(F)C(O)=O>[CH3:10][N:6]1[C:7]([O:8][CH3:9])=[C:3]([CH3:1])[C:4]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH3:19])[CH3:20])=[C:13]([CH3:21])[CH:12]=2)=[N:5]1

Participants

4

Reactant 2

HCID 70435TrimethylsilaneHCID 117724778HCID 117724778, compound

Product 1

HCID 117724701HCID 117724701, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

At 0° C., a mixture of 4-formyl-3-(4-isopropoxy-3-methyl-phenyl)-5-methoxy-1-methyl-1H-pyrazole (described in Reference Preparation example 97) 4.2 g and trifluoroacetic acid 20 ml was added trimethylsilane 4.2 g. The resulting mixture was stirred at room temperature for six hours, and the solvent was distilled off under reduced pressure, and thereto was added water 10 ml. 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 1,4-dimethyl-3-(4-isopropoxy-3-methyl-phenyl)-5-methoxy-1H-pyrazole 3.8 g.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionwas added water 10 ml
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-ed5a582ffabe428897c16f01ac69124b
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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