p-Fluoronitrobenzene → 5-[(4-nitrophenyl)-1,2,4-triazol-1-ylmethyl]-3,3-dimethyl-3H-isobenzofuran-1-one

HRID 1901761

Reaktionsgleichung

Reaktionsgleichung von HRID 1901761
[CH3:1][C:2]1([CH3:18])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][N:12]3[CH:16]=[N:15][CH:14]=[N:13]3)[CH:9]=2)[C:4](=[O:17])[O:3]1.CC(C)([O-])C.[K+].F[C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1>CN(C)C=O>[N+:32]([C:29]1[CH:30]=[CH:31][C:26]([CH:11]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[C:4](=[O:17])[O:3][C:2]3([CH3:18])[CH3:1])=[CH:27][CH:28]=1)([O-:34])=[O:33]

Komponenten

5

Edukt 3

HCID 9590p-FluoronitrobenzeneHCID 233686093,3-dimethyl-5-[1,2,4-triazol-1-ylmethyl]-3H-isobenzofuran-1-one2×HCID 23665647Potassium tert-butoxide

Produkt 1

HCID 233686115-[(4-nitrophenyl)-1,2,4-triazol-1-ylmethyl]-3,3-dimethyl-3H-isobenzofuran-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

3,3-Dimethyl-5-[1,2,4-triazol-1-ylmethyl]-3H-isobenzofuran-1-one (200 mg, Intermediate 1) was dissolved in N,N-dimethylformamide (8 ml) at 0° under nitrogen and potassium tert-butoxide was added (138 mg). After 30 minutes 4-fluoronitrobenzene (232 mg) in N,N-dimethylformamide (1 ml) was added and stirring continued for one hour. The mixture was warmed to room temperature, stirred for one hour then partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate then the combined organic extracts were washed with water, brine, dried then evaporated to a yellow solid. The crude material was purified by column chromatography on Merck 9385 silica eluting with dichloromethane:methanol (50:1) to give a yellow oil, 5-[(4-nitrophenyl)-1,2,4-triazol-1-ylmethyl]-3,3-dimethyl-3H-isobenzofuran-1-one.

Aufarbeitung

  1. stirringstirred for one hour
  2. customthen partitioned between water and ethyl acetate
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with water, brine
  5. customdried
  6. customthen evaporated to a yellow solid
  7. customThe crude material was purified by column chromatography on Merck 9385 silica eluting with dichloromethane:methanol (50:1)

Quellen und Nachweise

ORD-Eintrag
ord-2234c574978e42ff904f7d43ff18981b
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05578630

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