Ethyl orthoformate → 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazole

HRID 1531391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1531391
[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([NH:15][NH2:16])=[O:14])=[CH:11][CH:10]=2)[O:3]1.[CH:20](OCC)(OCC)OCC>C(O)C>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:19])([CH3:1])[O:3][B:4]([C:9]2[CH:18]=[CH:17][C:12]([C:13]3[O:14][CH:20]=[N:16][N:15]=3)=[CH:11][CH:10]=2)[O:5]1

Komponenten

4

Edukt 2

HCID 31214Ethyl orthoformateHCID 212539794-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide

Produkt 1

HCID 212539742-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

10 g (38 mmol) of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzohydrazide are dissolved in 30 g (20 mmol) of triethyl orthoformate, and the mixture is heated to reflux. The ethanol formed during the reaction is continuously removed by distillation. After the mixture has cooled, the product crystallizes out, is filtered off and washed with a little ethanol. Yield: 8.7 g (32 mmol, 84%). An analogous procedure is carried out using the compounds of the formula (II) shown in Table 4.

Aufarbeitung

  1. temperaturethe mixture is heated to reflux
  2. customis continuously removed by distillation
  3. temperatureAfter the mixture has cooled
  4. customthe product crystallizes out
  5. filtrationis filtered off
  6. washwashed with a little ethanol

Quellen und Nachweise

ORD-Eintrag
ord-3c79c8c679bc4b2d813165866d68f6b8
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06197967B1

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