Tetrahydrofuran → 1,2-Phenanthrenedione

HRID 2195578Notes

Reaction equation

HRID 2195578 reaction equation
[Si](O[CH:9]1[CH:22](O[Si](C(C)(C)C)(C)C)[C:21]2[C:20](=[O:31])[C:19](=[O:32])[CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(O)(=O)C>[C:20]1(=[O:31])[C:21]2[CH:22]=[CH:9][C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]=2[CH:17]=[CH:18][C:19]1=[O:32]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86639211HCID 86639211, compound

Product 1

HCID 30805661,2-PhenanthrenedioneYield 105.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a 20 mL volume glass container, 187 mg of the above-prepared 9,10-bis(t-butyldimethylsilyloxy)-9,10-dihydrophenanthrenequinone trimer, 20 mL of tetrahydrofuran, 64 μL of acetic acid, and 2.3 mL of tetrabutylammonium fluoride were placed 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 87 mg of a phenanthrenequinone compound represented by the following chemical structural formula (1b-2) (hereinafter referred to as a “phenanthrenequinone compound (1b-2)”) (yield 75%), 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-95efb3b403a74c36ae958c98a8b4ef03
Source dataset
uspto-grants-2012_12
Patent number
US08338027B2

Reaction notes

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