Methyl 3-(4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-4-methylbenzoate → Methyl 3-(4-cyano-1H-pyrazol-5-yl)-4-methylbenzoate

HRID 1488158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488158
[C:1]([C:3]1[CH:4]=[N:5][N:6](COCC[Si](C)(C)C)[C:7]=1[C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:11]([O:13][CH3:14])=[O:12])#[N:2]>C([SiH](CC)CC)C.FC(F)(F)C(O)=O>[C:1]([C:3]1[CH:4]=[N:5][NH:6][C:7]=1[C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:11]([O:13][CH3:14])=[O:12])#[N:2]

Komponenten

4

Edukt 1

HCID 90030276Methyl 3-(4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-4-methylbenzoate2×

Produkt 1

HCID 90030040Methyl 3-(4-cyano-1H-pyrazol-5-yl)-4-methylbenzoateAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6422Trifluoroacetic acidLösungsmittelHCID 12052TriethylsilaneLösungsmittel

Versuchsvorschrift

Into a 50-mL round-bottom flask, was placed a solution of methyl 3-(4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-4-methylbenzoate (compound 256.3, 1.9 g, 5.11 mmol) in triethylsilane (4 mL) and trifluoroacetic acid (8 mL). The resulting solution was stirred for 4 h at room temperature, then concentrated under reduced pressure. The pH of the residue was carefully adjusted to 7-8 with aqueous sodium bicarbonate (sat.), then the aqueous phase was extracted with ethyl acetate (2×100 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (20/1) as eluent to obtain the title compound as a white solid (600 mg, 49%).

Aufarbeitung

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationconcentrated under reduced pressure
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×100 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (20/1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-0435af20fbde4cfea6b95d7b0debf43c
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428502B2

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