Hydrochloric Acid → HCID 19808837, compound

HRID 374019Notes

Reaction equation

HRID 374019 reaction equation
[Mg].[CH3:2]I.[CH2:4]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[CH:13]=[C:12]1C(OCC)=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.C(O[CH2:31][CH3:32])C>O1CCCC1.O.C(OCC)(=O)C>[CH2:4]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[CH:13]=[C:12]1[C:31]([CH3:32])=[CH2:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 13295697Ethyl 1-benzyl-5-methoxy-1H-indole-2-carboxylate

Product 1

HCID 19808837HCID 19808837, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

8.95 g of magnesium was suspended in 160 ml of anhydrous diethyl ether. To the suspension was dropwise added 52.3 g of methyl iodide in 1 hour with stirring under refluxing. The resulting mixture was refluxed for 1 hour. Thereto was dropwise added a solution of 38 g of 1-benzyl-2-ethoxycarbonyl-5-methoxyindole dissolved in 110 ml of anhydrous tetrahydrofuran in 40 minutes at room temperature. The resulting mixture was refluxed for 1 hour and then cooled with ice cooling. Thereto was added 400 ml of ethyl acetate and to the resulting mixture was dropwise added 300 ml of water in 1 minute with stirring at 0° C. The resulting mixture was adjusted to pH 7.0 with diluted hydrochloric acid. The organic layer was separated, washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was dissolved in 190 ml of methylene chloride. To the solution was added 29.8 g of triethylamine, and to the resulting mixture was dropwise added 16.9 g of methanesulfonyl chloride in 20 minutes with stirring at 0° C. The resulting mixture was stirred for 20 minutes at room temeprature. The reaction mixture was washed with 1N hydrochloric acid, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in this order and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from acetonitrile to obtain 26.8 g (yield: 79%) of 1-benzyl-2-isopropenyl-5-methoxyindole as light yellow crystals.

Workup

  1. customin 1 hour
  2. temperatureunder refluxing
  3. temperatureThe resulting mixture was refluxed for 1 hour
  4. temperatureThe resulting mixture was refluxed for 1 hour
  5. temperaturecooled with ice cooling
  6. customin 1 minute
  7. stirringwith stirring at 0° C
  8. customThe organic layer was separated
  9. washwashed with an aqueous saturated sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. dissolutionThe residue was dissolved in 190 ml of methylene chloride
  13. additionTo the solution was added 29.8 g of triethylamine
  14. customin 20 minutes
  15. stirringwith stirring at 0° C
  16. stirringThe resulting mixture was stirred for 20 minutes at room temeprature
  17. washThe reaction mixture was washed with 1N hydrochloric acid
  18. dry with materialan aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in this order and dried over anhydrous magnesium sulfate
  19. customThe solvent was removed by distillation under reduced pressure
  20. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-0a898a2268db47ae9303e0889fdfc329
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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