Hydrochloric Acid → HCID 19024734, compound

HRID 1034060Notes

Reaction equation

HRID 1034060 reaction equation
C(C1C=CC(C(C2C=CC(CC(C)C)=CC=2)CC2C=C(C=CC=2)C(O)=O)=CC=1)C(C)C.[CH2:32]([C:36]1[CH:41]=[CH:40][C:39]([CH:42]([C:53]2[CH:58]=[CH:57][C:56]([CH2:59][CH:60]([CH3:62])[CH3:61])=[CH:55][CH:54]=2)[CH2:43][C:44]2[CH:45]=[C:46]([CH:50]=[CH:51][CH:52]=2)[C:47](Cl)=[O:48])=[CH:38][CH:37]=1)[CH:33]([CH3:35])[CH3:34].C(Cl)(=O)C(Cl)=O.[NH:69]1[C:77]2[C:72](=[CH:73][CH:74]=[CH:75][CH:76]=2)[CH:71]=[CH:70]1.C[Mg]Br.Cl>O1CCCC1.CCOCC.C(OCC)(=O)C>[CH2:32]([C:36]1[CH:41]=[CH:40][C:39]([CH:42]([C:53]2[CH:58]=[CH:57][C:56]([CH2:59][CH:60]([CH3:62])[CH3:61])=[CH:55][CH:54]=2)[CH2:43][C:44]2[CH:45]=[C:46]([CH:50]=[CH:51][CH:52]=2)[C:47]([C:71]2[C:72]3[C:77](=[CH:76][CH:75]=[CH:74][CH:73]=3)[NH:69][CH:70]=2)=[O:48])=[CH:38][CH:37]=1)[CH:33]([CH3:35])[CH3:34]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 798IndoleHCID 65578Oxalyl chlorideHCID 10787965HCID 10787965, compoundHCID 19024843HCID 19024843, compound2×HCID 178418573HCID 178418573, compound

Product 1

HCID 19024734HCID 19024734, compoundYield 34.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

3-[2,2-Bis(4-isobutylphenyl)ethyl]benzoic acid (1 g) was converted to 3-[2,2-bis(4-isobutylphenyl)ethyl]benzoyl chloride (1.13 g) with oxalyl chloride as an usual manner. To a solution of indole (0.918 g) in tetrahydrofuran (15 ml) was added 3M solution of methyl magnesium bromide in ether (3 ml) at 20° C., and the mixture was stirred at 20° C. for 1 hour. A solution of 3-[2,2-bis(4-isobutylphenyl)ethyl]benzoyl chloride (1.13 g) in tetrahydrofuran (15 ml) was added to the mixture at 20° C. After stirred at 20° C. for 1 hour, 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 (50 g) eluting with a mixture of hexane and ethyl acetate (20:1) to give 3-[3-[2,2-bis(4-isobutylphenyl)ethyl]benzoyl]indole (468 mg) as pale red crystals.

Workup

  1. stirringAfter stirred at 20° C. for 1 hour
  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 (50 g)
  7. washeluting with a mixture of hexane and ethyl acetate (20:1)

Sources & evidence

ORD record
ord-230d59aa6fcf4499805a0fd7ffdbcedd
Source dataset
uspto-grants-1994_05
Patent number
US05312829

Reaction notes

Loading…