Tetrahydrofuran → 1,2-Phenanthrenedione

HRID 2195577

Reaktionsgleichung

Reaktionsgleichung von HRID 2195577
[Si]([O:8][CH:9]1[CH:22]([O:23][Si](C(C)(C)C)(C)C)[C:21]2C=C(I)C=C[C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)(C(C)(C)C)(C)C.O1[CH2:36][CH2:35][CH2:34][CH2:33]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(O)C>[C:9]1(=[O:8])[C:10]2[CH:11]=[CH:12][C:13]3[C:14](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:15]=2[CH:16]=[CH:21][C:22]1=[O:23]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 685517879,10-Bis(t-butyldimethylsilyloxy)-2-iodo-9,10-dihydro-phenanthrene

Produkt 1

HCID 30805661,2-PhenanthrenedioneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Into a 20 mL volume eggplant-shaped flask, 80 mg of the above-prepared 9,10-bis(t-butyldimethylsilyloxy)-2-iodo-9,10-dihydro-phenanthrene dimer, 10 mL of tetrahydrofuran, 43 mg of ethanol, and 0.4 mL of tetrabutylammonium fluoride were added and stirred at room temperature in air. The resultant reaction mixture was allowed to stand. Thereafter, the precipitate was collected by filtration and washed, thereby to give 28 mg of a phenanthrenequinone compound represented by the following chemical structural formula (1b-1) (hereinafter referred to as a “phenanthrenequinone compound (1b-1)”) (yield 76%) as a reddish brown-colored solid.

Aufarbeitung

  1. customThe resultant reaction mixture
  2. filtrationThereafter, the precipitate was collected by filtration
  3. washwashed

Quellen und Nachweise

ORD-Eintrag
ord-9ca737a9f5214428ab90c08d96b3b452
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338027B2

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