Trimethylsilyl triflate → HCID 10357417, Verbindung

HRID 1654782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1654782
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[Br:13])[C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2].C[Si](C)(C)[O:17][CH:18](O[Si](C)(C)C)[CH3:19].C[Si](OS(C(F)(F)F)(=O)=O)(C)C>C(Cl)Cl>[CH2:18]1[O:17][C:9]2([C:10]3[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[C:12]([Br:13])[CH:11]=3)[CH2:7][CH2:8]2)[O:14][CH2:19]1

Komponenten

5

Edukt 3

HCID 65367Trimethylsilyl triflateHCID 100609406-bromo-5-nitro-2,3-dihydro-1H-inden-1-oneHCID 18183672HCID 18183672, Verbindung

Produkt 1

HCID 10357417HCID 10357417, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 5-nitro-6-bromo-1-indanone (11.0 g, 43 mmol) and bis(trimethylsilyloxy)ethane (22.0 mL, 90 mmol) in CH2Cl2 (90 mL) at room temperature was added trimethylsilyltrifluoromethanesulfonate (100 μL). The mixture was stirred for 2 h and the homogeneous solution was quenched with saturated aqueous NaHCO3 (100 mL). The CH2Cl2 layer was separated, washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. Chromatography over silica gel, eluting with ethyl acetate:hexanes (2:5), furnished 10.2 g (79%) of the title compound as a pale yellow solid.

Aufarbeitung

  1. customthe homogeneous solution was quenched with saturated aqueous NaHCO3 (100 mL)
  2. customThe CH2Cl2 layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. washChromatography over silica gel, eluting with ethyl acetate:hexanes (2:5)

Quellen und Nachweise

ORD-Eintrag
ord-5f5870a47b644ae68d7b679edc7fac00
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05409944

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