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Hydrofluoric Acid → Ethyl 4-methyl-1H-1,2,3-triazole-1-acetate

HRID 887156
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 887156
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:10]([Si](C)(C)C)=[C:9]([CH3:15])[N:8]=[N:7]1)[CH3:2].F>C1COCC1.O>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[CH:10]=[C:9]([CH3:15])[N:8]=[N:7]1)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 14917Hydrofluoric AcidHCID 66839489Ethyl [4-methyl-5-(trimethylsilyl)-1H-1,2,3-triazole-1-yl]acetate

Produkt 1

HCID 59603650Ethyl 4-methyl-1H-1,2,3-triazole-1-acetateAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 0.77 g (3.2 mmol) of ethyl [4-methyl-5-(trimethylsilyl)-1H-1,2,3-triazole-1-yl]acetate from step A above in 2 mL of THF was added 1.3 mL (32 mmol) of a solution of 50% hydrofluoric acid in water. The resulting mixture was stirred at room temperature for 3 h and then evaporated to dryness in vacuo. Next, 5 mL of a 2.0 N ammonia in methanol solution was added and then the mixture was again evaporated to dryness in vacuo. The mixture was dissolved in dichloromethane, filtered and then evaporated in vacuo to afford the title compound as a clear gum (0.51 g. 93%). 1HNMR (500 MHz, CDCl3) δ: 7.5 (s, 1H), 5.05 (s, 2H), 4.23 (m, 2H), 2.30 (s, 3H), 1.30 (m, 3H).

Aufarbeitung

  1. customevaporated to dryness in vacuo
  2. additionNext, 5 mL of a 2.0 N ammonia in methanol solution was added
  3. customthe mixture was again evaporated to dryness in vacuo
  4. dissolutionThe mixture was dissolved in dichloromethane
  5. filtrationfiltered
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dda2b115cdfa47b88fb057d298ca3e12
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08247415B2

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