Trifluoroacetic acid → HCID 60123707, Verbindung

HRID 1368068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1368068
[CH:1]1([C:4](=[O:7])[CH:5]=[CH2:6])[CH2:3][CH2:2]1.C(O[CH2:13][N:14]([CH2:23][Si](C)(C)C)[C@@H:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])CCC.FC(F)(F)C(O)=O>ClC(Cl)C>[CH:1]1([C:4]([CH:5]2[CH2:6][CH2:13][N:14]([C@@H:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:16])[CH2:23]2)=[O:7])[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 5349541-Cyclopropyl-2-propen-1-oneHCID 15701915HCID 15701915, Verbindung

Produkt 1

HCID 60123707HCID 60123707, VerbindungAusbeute 49,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

The product containing 1-cyclopropyl-2-propen-1-one described in Reference Example 1 (8.01 g) and N-(normal-butoxymethyl)-N-[1-(R)-phenylethyl]trimethylsilylmethylamine (23.2 g, 79.9 mmol) were dissolved in dry dichloroethane (350 ml) to which was subsequently added dropwise trifluoroacetic acid (500 μl). After 12 hours of stirring at room temperature, the reaction solution was washed with saturated sodium bicarbonate aqueous solution (100 ml) and saturated sodium chloride aqueous solution (100 ml) in that order. This was dried over anhydrous magnesium sulfate, filtered and then concentrated under a reduced pressure. The resulting residue was applied to a flash silica gel chromatography and eluted with n-hexane:ethyl acetate=2:1, thereby obtaining 9.08 g (49.6%) of the title compound as a colorless oil. In this connection, this product was obtained as a 1:1 diastereomer mixture.

Aufarbeitung

  1. washthe reaction solution was washed with saturated sodium bicarbonate aqueous solution (100 ml) and saturated sodium chloride aqueous solution (100 ml) in that order
  2. dry with materialThis was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under a reduced pressure
  5. washeluted with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-73df22791e25463bbcd4edd7f0910b76
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06573260B1

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