m,alpha-Dichlorotoluene → HCID 70240212, compound

HRID 1069618Notes

Reaction equation

HRID 1069618 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][C:7]=1[CH2:17][CH3:18])[CH3:2].[H-].[Na+].[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Cl>O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[C:23]([Cl:22])[CH:24]=2)[C:7]=1[CH2:17][CH3:18])[CH3:2]

Participants

5

Reactant 3

HCID 12103m,alpha-DichlorotolueneHCID 24758Sodium hydrideHCID 57203635HCID 57203635, compound

Product 1

HCID 70240212HCID 70240212, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Ethyl-5-methoxy-1H-indole-3-acetic acid ethyl ester (1.82 g, 7.4 mmol) was added to 296 mg (7.4 mmol) of NaH/mineral oil (previously washed with hexane), the mixture stirred for 0.5 hours and 0.93 mL (7.4 mmol) of 3-chlorobenzyl chloride added. After 21 hours, water was added and the mixture extracted with ethyl acetate. The ethyl acetate was washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 2.13 g (75% yield) of 1-[(3-chlorophenyl)methyl]-2-ethyl-5-methoxy-1H-indole-3-acetic acid ethyl ester as an oil.

Workup

  1. washpreviously washed with hexane), the mixture
  2. waitAfter 21 hours
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe ethyl acetate was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-afce7619f2034687b029054688049c9f
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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