HCID 13703687, compound → HCID 19710560, compound

HRID 2260381Notes

Reaction equation

HRID 2260381 reaction equation
Br[C:2]1[C:3](=[O:11])[C:4]([O:9][CH3:10])=[CH:5][C:6](=[O:8])[CH:7]=1.[Si](O[N:20]=[CH:21][CH:22]=[CH:23][CH3:24])(C(C)(C)C)(C)C>ClC1C=CC=CC=1>[CH3:10][O:9][C:4]1[C:3](=[O:11])[C:2]2[N:20]=[CH:21][CH:22]=[C:23]([CH3:24])[C:7]=2[C:6](=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 13703687HCID 13703687, compoundHCID 53919901HCID 53919901, compound

Product 1

HCID 19710560HCID 19710560, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

In a 50 mL round bottom flask 2-bromo-6-methoxy-1,4-benzoquinone (282 mg, 1.3 mmol) was dissolved in dry chlorobenzene (28 mL) along with 1-(tert-butyldimethylsilyloxy)-1-aza-1,3-pentadiene (130 mg, 0.65 mmol). The solution was stirred and heated to reflux for 4 days under N2. The dark reaction was allowed to cool and was added to a silica gel column (2.5×9 cm). The column was eluted with EtOAc/hexane (5:1) then EtOAc and finally ethanol. The solvent was removed, benzene was added, and the resulting mixture was heated and filtered to remove insoluble impurities. Evaporation of the filtrate gave 62 mg, 47% of the crude product. 1H NMR (CDCl3) δ2.76 (s, 3H), 3.93 (s, 3H), 6.20 (s, 1H), 7.52 (d, J=8 Hz, 8.30 (d, J=8 Hz, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 days under N2
  3. customThe dark reaction
  4. temperatureto cool
  5. additionwas added to a silica gel column (2.5×9 cm)
  6. washThe column was eluted with EtOAc/hexane (5:1)
  7. customThe solvent was removed
  8. additionbenzene was added
  9. temperaturethe resulting mixture was heated
  10. filtrationfiltered
  11. customto remove insoluble impurities
  12. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-3fc68cab131e48119b53ef5f0e0d7d20
Source dataset
uspto-grants-1995_12
Patent number
US05476933

Reaction notes

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