Trimethylsilylacetylene → 3-(4-Bromophenyl)-5-(trimethylsilyl)isoxazole

HRID 736394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 736394
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[N:7][OH:8])=[CH:4][CH:3]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[CH:16]=[C:15]([Si:12]([CH3:14])([CH3:13])[CH3:11])[O:8][N:7]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 6080884-Bromobenzaldehyde Oxime

Produkt 1

HCID 221704493-(4-Bromophenyl)-5-(trimethylsilyl)isoxazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The product from Example 42A (0.124 g, 0.621 mmol) and trimethylsilylacetylene (0.35 mL, 2.5 mmol) were combined in tetrahydrofuran (2.2 mL), treated bleach (2.2 mL), and stirred for 22 hours. The mixture was diluted with ethyl acetate (7 mL), washed with brine (5 mL), dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (7% ethyl acetate in hexanes) to provide the title compound.

Aufarbeitung

  1. additiontreated bleach (2.2 mL)
  2. washwashed with brine (5 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (7% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a508347bbb9b47cdaa96cfeffd488b18
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595332B2

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