2-chloro-8-hydroxy-1,4-naphthoquinone → HCID 68456956, compound

HRID 2358468Notes

Reaction equation

HRID 2358468 reaction equation
C[Si](C)(C)O[C:4]([CH3:20])=[C:5]([C:13]([O:15][Si](C)(C)C)=[CH2:14])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].Cl[C:24]1[C:25](=[O:36])[C:26]2[C:31]([C:32](=[O:34])[CH:33]=1)=[CH:30][CH:29]=[CH:28][C:27]=2[OH:35]>C1(C)C=CC=CC=1>[OH:15][C:13]1[C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([CH3:20])[C:24]2[C:25](=[O:36])[C:26]3[C:31]([C:32](=[O:34])[C:33]=2[CH:14]=1)=[CH:30][CH:29]=[CH:28][C:27]=3[OH:35]

Participants

4

Reactant 2

HCID 108567122-chloro-8-hydroxy-1,4-naphthoquinoneHCID 74082985HCID 74082985, compound

Product 1

HCID 68456956HCID 68456956, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.1 g (58.5 mmol, 2.0 eq.) of tert-butyl 3-trimethylsilanyloxy-2-(1-trimethylsilanyloxyvinyl)but-2-enate and 5.05 g (24.3 mmol) of 2-chloro-8-hydroxy-1,4-naphthoquinone (Giles & Roos, J. Chem. Soc Perkin 11976, 2057-2060) were dissolved in 125 ml of anhydrous toluene and heated at reflux for 24 hours. The solvent was then removed on a rotary evaporator, and 150 ml of THF were added to the brown oily residue. After the addition of 10 ml of water, the mixture was stirred at RT for 1d. About 50 ml of silica gel were then added, and the mixture was freed from the solvent. The crude product, absorbed on the silica gel, was then filled into a frit filled with silica gel and eluted using DCM as mobile phase. The product band, which has an intensive yellow color and is easy to isolate, was collected separately, and, after removal of the solvent, it was possible to isolate 3.8 g (10.9 mmol, 45%) of the brown tert-butyl 3,8-dihydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate which still contained small amounts of impurities; however, these could be removed completely in the next synthesis step.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. customThe solvent was then removed on a rotary evaporator, and 150 ml of THF
  4. additionwere added to the brown oily residue
  5. additionAfter the addition of 10 ml of water
  6. additionAbout 50 ml of silica gel were then added
  7. customThe crude product, absorbed on the silica gel
  8. additionwas then filled into a frit
  9. additionfilled with silica gel
  10. washeluted
  11. customto isolate
  12. customwas collected separately
  13. customafter removal of the solvent, it

Sources & evidence

ORD record
ord-8e2effd8a546477b99adf163a479633e
Source dataset
uspto-grants-2010_07
Patent number
US07763740B2

Reaction notes

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