Trifluoroacetic anhydride → 2-(2,4-Difluorophenyl)-5-methyl-2H-1,2,3-triazole-4-methanol

HRID 623709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 623709
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]([CH3:14])[C:11]([CH3:15])=[N+:10]1[O-].FC(F)(F)C(OC(=O)C(F)(F)F)=[O:20]>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]([CH2:14][OH:20])[C:11]([CH3:15])=[N:10]1

Komponenten

5

Edukt 2

HCID 9845Trifluoroacetic anhydrideHCID 901098102-(2,4-difluorophenyl)-4,5-dimethyl-2H-1,2,3-triazole 1-oxide2×

Produkt 1

HCID 901092522-(2,4-Difluorophenyl)-5-methyl-2H-1,2,3-triazole-4-methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 2-(2,4-difluorophenyl)-4,5-dimethyl-2H-1,2,3-triazole 1-oxide (i.e. the product of Step A, 1.78 g, 7.0 mmol) in tetrahydrofuran (14 mL) was added trifluoroacetic anhydride (2.5 mL, 17.5 mmol). The reaction mixture was stirred at 110° C. in the microwave for 75 min. The mixture was diluted with ethyl acetate, washed successively with 1.0 M aqueous sodium hydroxide and 50% aqueous sodium hydroxide, dried (MgSO4) and concentrated under reduced pressure to afford the crude product. The crude material was purified by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to obtain the title compound (0.59 g) as a colorless solid.

Aufarbeitung

  1. washwashed successively with 1.0 M aqueous sodium hydroxide and 50% aqueous sodium hydroxide
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product
  5. customThe crude material was purified by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9ac76b9069f9454cbc7121c5c424d5ac
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302999B2

Notizen zur Reaktion

Wird geladen…