1-Methylfluorene → HCID 15045094, Verbindung

HRID 1089852Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1089852
[CH3:1][C:2]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Li][CH2:16][CH2:17][CH2:18]C.BrC1[O:25][CH2:24][CH2:23][O:22]1.C(OCC)(=O)C.CCCCCC>C1COCC1>[CH3:1][C:2]1[C:14]2[CH:13]([CH2:18][CH2:17][CH:16]3[O:25][CH2:24][CH2:23][O:22]3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 156041-MethylfluoreneHCID 143725662-Bromo-1,3-dioxolaneHCID 21226206Ethyl acetate hexaneHCID 178418339Butyllithium

Produkt 1

HCID 15045094HCID 15045094, VerbindungAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

1-Methylfluorene (3.2 g, 18.0 mmol) in 50 mL THF was charged with BuLi, 2.35M solution in hexanes (7.65 mL, 18.0 mmol) at -78° C. The reaction mixture was stirred for 2 hr at -78° C. then 2-bromo-1.3-dioxolane (3.6 g, 19.8 mmol) was added by a syringe. The reaction was monitored by TLC (silica, 10% ethyl acetate/hexane). The reaction mixture was stirred for 2 hr at room temperature then the THF was evaporated. The residue was dissolved in ethyl acetate. The solution was washed with water, dried over magnesium sulfate, treated with a coarse silica gel and Norit and evaporated to yield 4.8 g (96.6%) of the desired product.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 2 hr at room temperature
  2. customthe THF was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with a coarse silica gel and Norit
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6835f0d10da447f0909bd007befd7676
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05079260

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