Triphenylphosphine → 1-Methyl-5-{2-[4-(trifluoromethyl)phenoxy]ethyl}-1H-pyrazole

HRID 238391

Reaktionsgleichung

Reaktionsgleichung von HRID 238391
[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][OH:9])=[CH:5][CH:4]=[N:3]1.O[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.O1CCCC1>[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][O:9][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=[N:3]1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 218324192-(1-methyl-1H-pyrazol-5-yl)ethan-1-ol

Produkt 1

HCID 895587031-Methyl-5-{2-[4-(trifluoromethyl)phenoxy]ethyl}-1H-pyrazoleAusbeute 54,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2-(1-methyl-1H-pyrazol-5-yl)ethanol (1.00 g), 4-hydroxybenzotrifluoride (2.57 g), 1.9 M diisopropyl azodicarboxylate (6.26 mL, toluene solution), triphenylphosphine (3.12 g) and tetrahydrofuran (50 mL) was stirred at a room temperature for 2 days. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with water, and was then dried over anhydrous sodium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=90:10 to 55:45), so as to obtain the title compound (1.17 g) in the form of a light yellow oily substance.

Aufarbeitung

  1. extractionthe obtained mixture was then extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by vacuum concentration
  5. customThe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=90:10 to 55:45)

Quellen und Nachweise

ORD-Eintrag
ord-ad54ccf442e04ba5aae94821068c84c9
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642626B2

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