Isobutylene oxide → 2-methyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-ol

HRID 18953

Reaktionsgleichung

Reaktionsgleichung von HRID 18953
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH3:15][C:16]1([CH3:19])[CH2:18][O:17]1>CN(C)C=O.O>[CH3:15][C:16]([OH:17])([CH3:19])[CH2:18][N:6]1[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]1

Komponenten

6

Edukt 3

HCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 178526745HCID 178526745, Verbindung

Produkt 1

HCID 545944402-methyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-olAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 3-nitro-1H-pyrazole (200 mg, 1.77 mmol) in N,N-dimethylformamide (5 mL) was treated with solid potassium carbonate (352 mg, 2.55 mmol) and 2,2-dimethyl-oxirane (3.14 mL, 3.54 mmol) and placed in a sealed tube and heated at 100° C. for 1 h in an oil bath. After this time the reaction was cooled to 25° C. and diluted with water (10 mL) and extracted with ethyl acetate (3×10 mL). The organic layers were then combined and dried over sodium sulfate, filtered and concentrated in vacuo. Purification by AnaLogix Intelliflash system (12 g column, 50% ethyl acetate/hexanes to 60% ethyl acetate/hexanes) afforded 2-methyl-1-(3-nitro-pyrazol-1-yl)-propan-2-ol (175 mg, 54%) as a clear colorless oil: ES-HRMS m/z calculated for C7H11N3O3 [M+H]+ 186.0873, observed 186.0873; 1H NMR (300 MHz, CDCl3) δ ppm 1.25 (s, 6H), 2.11 (br. s., 1H), 4.18 (s, 2H), 6.92 (d, J=2.4 Hz, 1H), 7.60 (d, J=2.4 Hz, 1H).

Aufarbeitung

  1. customplaced in a sealed tube
  2. temperatureAfter this time the reaction was cooled to 25° C.
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by AnaLogix Intelliflash system (12 g column, 50% ethyl acetate/hexanes to 60% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e421808bbb25483d93ddb3855be4b1a4
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741327B2

Verknüpfte Notizen

Wird geladen…