Potassium Carbonate → Methyl [(5-nitro-1,2-benzisoxazol-3-yl)oxy]acetate

HRID 1274561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1274561
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][N:10]=[C:9]([OH:12])[C:8]=2[CH:13]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]([O:24][CH3:25])=[O:23]>CN(C)C=O>[CH3:25][O:24][C:22](=[O:23])[CH2:21][O:12][C:9]1[C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[O:11][N:10]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178526505HCID 178526505, Verbindung

Produkt 1

HCID 53638345Methyl [(5-nitro-1,2-benzisoxazol-3-yl)oxy]acetateAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5-nitro-1,2-benzisoxazol-3-ol (3.90 g, 0.0220 mol) and potassium carbonate (4.17 g, 0.0300 mol) in N,N-dimethylformamide is stirred for 30 minutes, treated with methyl bromoacetate (3.96 g, 0.0260 mol), stirred overnight at room temperature, and poured into an acidic ice-water mixture. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a yellow oil. Column chromatography of the oil using silica gel and a (1:1) to (4:1) methylene chloride/hexanes gradient gives the title product as a white solid (2.80 g, mp 72-73.5° C.) which is identified by NMR spectral analyses.

Aufarbeitung

  1. stirringstirred overnight at room temperature
  2. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  3. washwashed sequentially with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-564a0d0d63f044ad864aef4685cac5b6
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06156700

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