Pinacol → 1-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 1528074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1528074
[C:1]1([N:7]2[C:11]([B:12]([OH:14])[OH:13])=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[C:16]([C:19](O)([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C1(C)C=CC=CC=1.ClCCl>[C:1]1([N:7]2[C:11]([B:12]3[O:13][C:19]([CH3:21])([CH3:20])[C:16]([CH3:18])([CH3:17])[O:14]3)=[CH:10][CH:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 6425PinacolHCID 59436217(1-phenyl-1H-pyrazol-5-yl)boronic acid

Produkt 1

HCID 580723671-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

(1-Phenyl-1H-pyrazol-5-yl)boronic acid (25.0 g) was dissolved in toluene (700 mL), pinacol (18.0 g) was added thereto at room temperature, and the mixture was stirred at 40° C. for 2 days. The reaction mixture was diluted with dichloromethane, and the mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting solid was collected by filtration, and washed with hexane to give the title compound (19.8 g).

Aufarbeitung

  1. washthe mixture was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-b7492c04d9b1403cbbc0d80455f72b9f
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090586B2

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