Trimethylaluminum → HCID 86725332, Verbindung

HRID 925218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 925218
[CH2:1]([O:3][C:4]([N:6]1[CH2:23][CH2:22][C:10]2[C:11]3[C:12](Cl)([CH3:20])[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:24][Al](C)C>C1CCCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:23][CH2:22][C:10]2[C:11]3[C:12]([CH3:24])([CH3:20])[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 16682925TrimethylaluminumHCID 86725330HCID 86725330, Verbindung

Produkt 1

HCID 86725332HCID 86725332, VerbindungAusbeute 9,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8078CyclohexaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Into a glass vial the product from step (b) (214 mg, 0.623 mmol) dissolved in cyclohexane (3 ml) was added. To this solution, AlMe3 (2M in hexanes, 1.2 ml, 2.49 mmol) was added. The reaction mixture was heated to 80° C. and stirred for 1 hour. The reaction mixture was allowed to cool to room temperature and was quenched by the addition of 2M HCl (20 ml). The aqueous mixture was extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the crude product. Purification by silica-gel chromatography (gradient elution: 0 to 20% EtOAc in hexanes) gave the sub-title compound as an orange oil (20 mg). NMR (300 MHz, CDCl3) δ 6.99 (s, 2H); 4.15 (q, J=7.2 Hz, 2H); 3.62-3.59 (m, 4H); 3.29 (t, J=14.1 Hz, 2H); 3.01-2.91 (m, 2H); 1.39 (s, 6H); 1.26 (t, J=7.2 Hz, 3H); MS: ESI (positive): 324 (M+1).

Aufarbeitung

  1. additionwas added
  2. temperatureto cool to room temperature
  3. customwas quenched by the addition of 2M HCl (20 ml)
  4. extractionThe aqueous mixture was extracted with EtOAc (3×)
  5. washThe combined EtOAc extracts were washed with brine
  6. dry with materialdried over Na2SO4, and solvent
  7. customevaporated in vacuo
  8. customto give the crude product
  9. customPurification
  10. washby silica-gel chromatography (gradient elution: 0 to 20% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3caf3f0b9150487ab1bd70a04c7ce2a6
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284277B2

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