Hydrochloric Acid → HCID 19024724, compound

HRID 249153Notes

Reaction equation

HRID 249153 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]Br.[CH2:13]([C:17]1[CH:22]=[CH:21][C:20]([CH:23]([C:34]2[CH:39]=[CH:38][C:37]([CH2:40][CH:41]([CH3:43])[CH3:42])=[CH:36][CH:35]=2)[CH2:24][C:25]2[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)[CH:14]([CH3:16])[CH3:15].Cl>O1CCCC1.CCOCC.C(OCC)(=O)C>[CH2:40]([C:37]1[CH:38]=[CH:39][C:34]([CH:23]([C:20]2[CH:19]=[CH:18][C:17]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:22][CH:21]=2)[CH2:24][C:25]2[CH:33]=[CH:32][C:28]([C:29]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)=[O:30])=[CH:27][CH:26]=2)=[CH:35][CH:36]=1)[CH:41]([CH3:43])[CH3:42]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 798IndoleHCID 19024785HCID 19024785, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 19024724HCID 19024724, compoundYield 16.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of indole (366 mg) in tetrahydrofuran (5 ml) was added 3M solution of methyl magnesium bromide in ether (1.5 ml) at 20° C., and the mixture was stirred at 20° C. for 1 hour. A solution of 4-[2,2-bis(4-isobutylphenyl)ethyl]benzoyl chloride (450 mg) in tetrahydrofuran (5 ml) was added to the mixture at 20° C. After stirred at 20° C. for 30 minutes, the mixture was poured into a mixture of 1N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water, aqueous sodium bicarbonate and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (10 g) eluting with a mixture of hexane and ethyl acetate (20:1) to give 3-[4-[2,2-bis(4-isobutylphenyl)ethyl]benzoyl]indole (90 mg) as colorless crystals.

Workup

  1. stirringAfter stirred at 20° C. for 30 minutes
  2. customThe organic layer was separated
  3. washwashed with water, aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by column chromatography on silica gel (10 g)
  7. washeluting with a mixture of hexane and ethyl acetate (20:1)

Sources & evidence

ORD record
ord-cc1a803bd5c8427db54ee748d1228f40
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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