Imidazole → 6-Triisopropylsilanyloxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester

HRID 556345

Reaktionsgleichung

Reaktionsgleichung von HRID 556345
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:2].N1C=CN=C1.Cl[Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[CH:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 136216618Ethyl 6-hydroxybenzo[d]isoxazole-3-carboxylate

Produkt 1

HCID 669926156-Triisopropylsilanyloxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 0.80 g (3.86 mMol) 6-hydroxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester [preparation see: J. Am. Chem. Soc. 97 (1974), 7305] in 8 ml DMF, 1.16 g (17 mMol) imidazol and 2.15 ml chlortriisopropylsilane (95%; 9.7 mMol) are added. After 50 min, the mixture is poured into ice-water and extracted twice with EtOAc. The organic phases are washed with 10% citric acid solution, 2× water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; hexane/EtOAc 29:1) gives the title compound: MS: [M+1]+=364; TLC(hexane/EtOAc 9:1): Rf=0.5.

Aufarbeitung

  1. extractionextracted twice with EtOAc
  2. washThe organic phases are washed with 10% citric acid solution, 2× water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f1d8cb9c60944259a2f2fc0480aead4a
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058276B2

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