HCID 13703687, compound → HCID 10655754, compound

HRID 2260380Notes

Reaction equation

HRID 2260380 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]=[C:21]([CH3:24])[CH:22]=[CH2:23])(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]=[C:21]([CH3:24])[CH:22]=[CH:23][C:7]=2[C:6](=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 13703687HCID 13703687, compoundHCID 54045980HCID 54045980, compound

Product 1

HCID 10655754HCID 10655754, compoundYield 57%

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)-2-methyl-1-aza-1,3-butadiene (130 mg, 0.65 mmol). The solution was stirred and heated to reflux for 22 h 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 75 mg, 57% of the crude product. 1H NMR (CDCl3) δ2.81 (s, 3H), 3.92 (s, 3H), 6.18 (s, 1H), 7.44 (d, J=5 Hz, 1H) 8.80 (d, J=5 Hz, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 22 h 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-c45468b140564d44bbc66f0fce910e11
Source dataset
uspto-grants-1995_12
Patent number
US05476933

Reaction notes

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