3-Cyanophenol → Ethyl[4-(3-Hydroxyphenyl)-1H-1,2,3-triazol-1-yl]acetate

HRID 82312

Reaktionsgleichung

Reaktionsgleichung von HRID 82312
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].[OH:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#N.O=[C:20]1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>C(O)(C)(C)C.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][N:1]1[CH:20]=[C:14]([C:13]2[CH:16]=[CH:17][CH:18]=[C:11]([OH:10])[CH:12]=2)[N:3]=[N:2]1)[CH3:9]

Komponenten

7

Edukt 3

HCID 133943-CyanophenolHCID 69480Acetic acid, azido-, ethyl esterHCID 23667548Sodium Ascorbate

Produkt 1

HCID 70847799Ethyl[4-(3-Hydroxyphenyl)-1H-1,2,3-triazol-1-yl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24462Copper SulfateKatalysatorHCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

Ethyl azidoacetate (14.9 g, 115 mmol) was dissolved in tert-butanol (200 mL), and 95% 3-hydroxybenzonitrile (13.7 g, 110 mmol) was added. A solution of sodium ascorbate (2.18 g, 11 mmol) in water (100 mL) was added, followed by a 0.3 M solution of copper sulfate under argon. The mixture was stirred at room temperature for 12 hours. The solution was evaporated to dryness in vacuo, the residue was dissolved in EtOAc (100 mL), dried (MgSO4), filtered, evaporated in vacuo to give the title compound as brown crystals in ˜100% (27.7 g) yield.

Aufarbeitung

  1. customThe solution was evaporated to dryness in vacuo
  2. dissolutionthe residue was dissolved in EtOAc (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6ebff5c06872415e8a04b5610978f174
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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