Methanol → Fluconazole

HRID 10762

Reaktionsgleichung

Reaktionsgleichung von HRID 10762
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([O:22][Si](C)(C)C)([CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.CO.[OH-].[Na+]>O>[CH:5]1[C:6]([F:8])=[CH:7][C:2]([F:1])=[C:3]([C:9]([OH:22])([CH2:10][N:11]2[N:12]=[CH:13][N:14]=[CH:15]2)[CH2:16][N:17]2[N:18]=[CH:19][N:20]=[CH:21]2)[CH:4]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 112918881,1′-[2-(2,4-Difluorophenyl)-2-[(trimethylsilyl)oxy]-1,3-propanediyl]bis[1H-1,2,4-triazole]

Produkt 1

HCID 3365FluconazoleAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 7.5 g (0.02 mol) of 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazole-1-yl)-2-(trimethylsilyloxy)propane, 40 ml of methanol, 3 ml of water and 0.1 g of sodium hydroxide was stirred at room temperature for 1 h. After adding 300 ml of water the solution was concentrated to a volume of 50 ml with vacuum distillation. The obtained suspension was cooled to 0° C. and filtered. The obtained product was 6.12 g, water content was 11.5%. After drying at 80° C. 5.35 g of title compound was obtained. Yield: 87.4%. Mp.: 139–141° C.

Aufarbeitung

  1. concentrationwas concentrated to a volume of 50 ml with vacuum distillation
  2. temperatureThe obtained suspension was cooled to 0° C.
  3. filtrationfiltered
  4. customAfter drying at 80° C

Quellen und Nachweise

ORD-Eintrag
ord-2b91f17c041f48b492f8978539c07591
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094904B2

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