Indole → Ketone, indol-3-yl p-methoxyphenyl (6CI,8CI)

HRID 247551Notes

Reaction equation

HRID 247551 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C[Mg]I.[C:13](Cl)(=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1>CCOCC>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[O:22])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 798IndoleHCID 7477p-Anisoyl chlorideHCID 178418373HCID 178418373, compound

Product 1

HCID 211017Ketone, indol-3-yl p-methoxyphenyl (6CI,8CI)

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

30 ml of ether solution containing 4.0 g of indole were added to 10 ml of ether solution containing 5.0 g of methylmagnesium iodide. And then 30 ml of ether solution containing 5.7 g of anisoyl chloride were added dropwise to the solution. The reaction mixture was allowed to stand for several hours and further refluxed for 3 hours. After cooling, the reaction mixture was washed with aqueous solution of sodium hydrogencarbonate. The obtained organic layer was evaporated to dryness under reduced pressure. After purification by chromatography on silica gel and recrystallization from ethanol, 3-(p-methoxybenzoyl)indole (compound 1) was obtained in the form of white crystals. (Yield: 42%)

Workup

  1. additionwere added dropwise to the solution
  2. waitto stand for several hours
  3. temperaturefurther refluxed for 3 hours
  4. temperatureAfter cooling
  5. washthe reaction mixture was washed with aqueous solution of sodium hydrogencarbonate
  6. customThe obtained organic layer was evaporated to dryness under reduced pressure
  7. customAfter purification by chromatography
  8. customon silica gel and recrystallization from ethanol

Sources & evidence

ORD record
ord-654df088391c4892a801d584e25a06a9
Source dataset
uspto-grants-1987_11
Patent number
US04708961

Reaction notes

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