Ammonium Persulfate → HCID 22117145, compound

HRID 1275539Notes

Reaction equation

HRID 1275539 reaction equation
[C:1]([O:9][C:10]1[C:11](=[O:21])[C:12]2[C:17]([C:18](=[O:20])[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][Si:23]([CH:26](C)[C:27](O)=O)([CH3:25])[CH3:24].S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>C(#N)C.O.C(OCC)C.[N+]([O-])([O-])=O.[Ag+]>[C:1]([O:9][C:10]1[C:11](=[O:21])[C:12]2[C:17]([C:18](=[O:20])[C:19]=1[CH2:27][CH2:26][Si:23]([CH3:25])([CH3:24])[CH3:22])=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 62648Ammonium PersulfateHCID 825051HCID 825051, compoundHCID 12218619HCID 12218619, compound

Product 1

HCID 22117145HCID 22117145, compoundYield 46.4%

Reagents, catalysts & solvents 4

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

2-Benzoyloxy-1,4-naphthoquinone (1.39 g, 5 mmol), trimethylsilylpropionic acid (1.09 g, 7.5 mmol) and silver nitrate (523 mg, 3 mmol) were suspended in 40 ml aqueous acetonitrile (1:1) and then heated to 65° C. Ammonium persulphate (1.71 g, 7.5 mmol) in 20 ml water was added slowly and dropwise over 30 minutes to the mixture. The reaction mixture was stirred at this temperature for a further hour and then cooled, diluted with diethyl ether and the aqueous phase removed. The organic extract was washed with saturated sodium bicarbonate solution, then brine and dried over anhydrous magnesium sulphate. After concentration in vacuo, the crude material was chromatographed using petroleum ether/ethyl acetate as eluent to give 2-benzoyloxy-3-(2'-trimethylsilylethyl)-1,4-naphthoquinone (879 mg) which was recrystallised from methanol, m.pt.: 92-95° C. NMR peaks at: 184.4, 178.2, 150.3, 142.6, 134.0, 133.8, 132.1, 130.9, 126.6, 126.6; 18.8, 16.2; -2.0; 163.8, 128.0, 128.7, 130.4, 134.2 (PhCO).

Workup

  1. temperaturecooled
  2. customthe aqueous phase removed
  3. extractionThe organic extract
  4. washwas washed with saturated sodium bicarbonate solution
  5. dry with materialbrine and dried over anhydrous magnesium sulphate
  6. concentrationAfter concentration in vacuo
  7. customthe crude material was chromatographed

Sources & evidence

ORD record
ord-e68e4fa1be104e00b5ec9c0d5fb52ed6
Source dataset
uspto-grants-2000_12
Patent number
US06162799

Reaction notes

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