1,2-Dichloroethane → HCID 19088070, compound

HRID 1646805Notes

Reaction equation

HRID 1646805 reaction equation
ClCCCl.[CH3:5][C:6]1[C:7]([OH:15])=[C:8]([CH3:14])[C:9]([CH3:13])=[C:10]([CH:12]=1)[OH:11].O[CH:17]([C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH:37]=[CH:36][N:35]=[CH:34]2)=[CH:29][CH:28]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24].B(F)(F)F.CCOCC>O.CO>[N:33]1([C:30]2[CH:29]=[CH:28][C:27]([CH:17]([C:12]3[C:10](=[O:11])[C:9]([CH3:13])=[C:8]([CH3:14])[C:7](=[O:15])[C:6]=3[CH3:5])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:32][CH:31]=2)[CH:37]=[CH:36][N:35]=[CH:34]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8000Boron trifluoride etherateHCID 12785TrimethylhydroquinoneHCID 19088079HCID 19088079, compound

Product 1

HCID 19088070HCID 19088070, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1,2-Dichloroethane (15 ml) was added to 0.76 g (5.0 mmole) of trimethylhydroquinone and 1.51 g (5.0 mmole) of methyl 7-hydroxy-7-[4-(1-imidazolyl)phenyl]heptanoate, followed by warming at 80° C. and stirring. 1.42 ml (5.0×2.3 mmole) of boron trifluoride ethyl etherate was added dropwise to the mixture, followed by stirring at 80° C. for 2 hours. Then, methanol (15 ml) was added to the reaction solution, followed by further stirring at 80° C. for 2 hours. After cooling by standing at room temperature, the solvent was distilled off, and the residue was dissolved in tetrahydrofuran (20 ml). A solution of 2.7 g (10.0 mmole) of ferric chloride in water (10 ml) was added to the solution, followed by stirring at room temperature for 20 minutes. The tetrahydrofuran was distilled off, and chloroform was added to the residue to conduct extraction. The organic layer was separated out, washed with aqueous sodium hydrogencarbonate solution added, then washed with aqueous sodium chloride solution, dried (magnesium sulfate) and evaporated. The residue was chromatographed on a silica gel column, and elution was effected with ethyl acetate. The fractions containing the object compound were collected, and the solvent was distilled off under reduced pressure to give 1.70 g (78%) of methyl 7-[4-(1-imidazolyl)phenyl]-7-(3,5,6-trimethyl-1,4-benzoquinon -2-yl)heptanoate.

Workup

  1. stirringby stirring at 80° C. for 2 hours
  2. stirringby further stirring at 80° C. for 2 hours
  3. temperatureAfter cooling
  4. customby standing at room temperature
  5. distillationthe solvent was distilled off
  6. dissolutionthe residue was dissolved in tetrahydrofuran (20 ml)
  7. stirringby stirring at room temperature for 20 minutes
  8. distillationThe tetrahydrofuran was distilled off
  9. additionchloroform was added to the residue
  10. extractionextraction
  11. customThe organic layer was separated out
  12. washwashed with aqueous sodium hydrogencarbonate solution
  13. additionadded
  14. washwashed with aqueous sodium chloride solution
  15. dry with materialdried (magnesium sulfate)
  16. customevaporated
  17. customThe residue was chromatographed on a silica gel column, and elution
  18. additionThe fractions containing the object compound
  19. customwere collected
  20. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e6ff74a4fad04b1bbaf8fc459a70ba8d
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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