Tetrahydrofuran → 1,2-Phenanthrenedione

HRID 2195577

Reaction equation

HRID 2195577 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 30805661,2-PhenanthrenedioneYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-9ca737a9f5214428ab90c08d96b3b452
Source dataset
uspto-grants-2012_12
Patent number
US08338027B2

Linked notes

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