Water → HCID 22506825, compound

HRID 985588Notes

Reaction equation

HRID 985588 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:15])[C:9]([OH:14])=[CH:10][C:11]=2[CH3:13])[CH2:6][CH:5]1[CH3:16])(=[O:3])[CH3:2].Cl[CH2:18][C:19]([CH3:21])=[CH2:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:15])[C:9]([O:14][CH2:20][C:19]([CH3:21])=[CH2:18])=[CH:10][C:11]=2[CH3:13])[CH2:6][CH:5]1[CH3:16])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 22506868HCID 22506868, compound

Product 1

HCID 22506825HCID 22506825, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-acetyl-2,3-dihydro-5-hydroxy-2,4,7-trimethyl-1H-indole (3.3 g, 16.1 mmol), 3-chloro-2-methyl-1-propene (2.6 g, 28.7 mmol) and potassium carbonate (3.5 g, 25.3 mmol) in dimethylformamide (25 ml) was stirred for 20 hours at 80° C. under nitrogen atmosphere. The reaction mixture was combined with water, and extracted twice with ethyl acetate. The organic layers were combined, washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to obtain 3.8 g of the title compound.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washwashed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-c80da7543d594413b9a89d0aecd2a713
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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