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Benzoyl chloride → Methyl 3-[N-(p-chlorobenzyl)-3-benzoyl-5-benzoyloxyindol-2-yl]-2,2-dimethylpropanoate

HRID 327227
Notes
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Reaction equation

HRID 327227 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:4][CH:3]=1.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][C:27](=[O:34])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:13][CH:14]=3)[C:9]([C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:8]2[CH2:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 14980565Methyl 3-[N-(p-chlorobenzyl)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate

Product 1

HCID 18947606Methyl 3-[N-(p-chlorobenzyl)-3-benzoyl-5-benzoyloxyindol-2-yl]-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 111,2-Dichloroethane
Solvent

Conditions

Temperature
80 °C

Procedure

Methyl 3-[N-(p-chlorobenzyl)-5-hydroxy indol-2-yl]-2,2-dimethylpropanoate (609 mg) from Example 8 (Step A) was dissolved in 10 mL of 1,2-dichloroethane and the solution charged with 0.5 mL of benzoyl chloride and 680 mg of AlCl3. The reaction was heated to 80° C. under argon for 1.5 h, then quenched with 20 mL of 0.5N Na, K tartrate solution, extracted with 3×20 mL of ether, washed with 10 mL of H2O and dried (MgSO4). Removal of solvent provided an oily residue which was chromatographed on silica gel to give the title compound.

Workup

  1. customquenched with 20 mL of 0.5N Na, K tartrate solution
  2. extractionextracted with 3×20 mL of ether
  3. washwashed with 10 mL of H2O
  4. dry with materialdried (MgSO4)
  5. customRemoval of solvent
  6. customprovided an oily residue which
  7. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-310dc547ee8841429e7eaa1fd5c7edf9
Source dataset
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05272145

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes