Chloroform → HCID 15675231, compound

HRID 1090123Notes

Reaction equation

HRID 1090123 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([CH3:24])=[CH:12][N:13]2C(OC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].C(Cl)(Cl)Cl>CO.O>[CH2:1]([O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([CH3:24])=[CH:12][NH:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 14797Potassium HydroxideHCID 15675236HCID 15675236, compound

Product 1

HCID 15675231HCID 15675231, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

The 4-benzyloxy-5-methoxy-1-methoxycarbonyl-3-methylindole (5.3 g) was dissolved in methanol (60 ml). A solution of potassium hydroxide (40.0 g) in water (60 ml) was added to the solution, and the mixture was heated under reflux for 2 hours. The reaction mixture was poured into water, and chloroform extraction was conducted. The extract was washed with saturated saline and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Wako Gel C-200, 100 g). Elution with chloroform gave 4-benzyloxy-5-methoxy-3-methylindole (4.3 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. washThe extract was washed with saturated saline
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Wako Gel C-200, 100 g)
  7. washElution with chloroform

Sources & evidence

ORD record
ord-15cdbec1d53744faa57a54365efd6721
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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