Water → HCID 22238069, compound

HRID 1743390Notes

Reaction equation

HRID 1743390 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:12])[C:10]=1[CH3:11])[N:7]([CH:13]=[O:14])[CH2:6][CH2:5]2.Cl[CH2:16][C:17]([CH3:19])=[CH2:18].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:11][C:10]1[C:9]([CH3:12])=[C:8]2[C:4]([CH2:5][CH2:6][N:7]2[CH:13]=[O:14])=[CH:3][C:2]=1[O:1][CH2:18][C:17]([CH3:19])=[CH2:16]

Participants

6

Reactant 4

HCID 962WaterHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 22238070HCID 22238070, compound

Product 1

HCID 22238069HCID 22238069, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 2,3-dihydro-5-hydroxy-6,7-dimethyl-1H-indole-1-carbaldehyde (21.8 g, 0.11 mol), 3-chloro-2-methyl-1-propene (15 mL, 0.15 mol) and potassium carbonate (23.6 g, 0.17 mol) in DMF (200 mL) was stirred at 60° C. for 15 hours under the nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate four times. The combined organic layers were washed with water and saturated brine, dried over magnesium sulfate, treated with active carbon, filtered, and concentrated under reduced pressure. The residue was recrystallized from diisopropyl ether-hexane to obtain 20.6 g of title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate four times
  2. washThe combined organic layers were washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. additiontreated with active carbon
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-9e3fc21bf586476fbfa73d6aa9281dcd
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

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