3-Chloro-2-methyl-1-propene → HCID 22506841, compound

HRID 985573Notes

Reaction equation

HRID 985573 reaction equation
[OH:1][C:2]1[C:3]([CH3:16])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([CH:12]=[O:13])[C:6]([CH3:15])([CH3:14])[CH2:5]2.[H-].[Na+].Cl[CH2:20][C:21]([CH3:23])=[CH2:22].[Cl-].[NH4+]>CN(C=O)C>[CH3:15][C:6]1([CH3:14])[CH2:5][C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=[C:2]([O:1][CH2:22][C:21]([CH3:23])=[CH2:20])[C:3]=2[CH3:16])[N:7]1[CH:12]=[O:13]

Participants

6

Reactant 4

HCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22506840HCID 22506840, compound

Product 1

HCID 22506841HCID 22506841, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-dihydro-5-hydroxy-2,2,4,7-tetramethyl-1H-indole-1-carbaldehyde (2.29 g, 10.4 mmol) in DMF (15 ml) was added 60% dispersion of sodium hydride in oil (0.42 g, 12 mmol) with cooling on ice and stirred under nitrogen atmosphere at the same temperature for 5 minutes. To the resulting mixture was added 3-chloro-2-methyl-1-propene (1.3 ml, 13 mmol) and stirred at room temperature for 30 minutes and at 60° C. for 15 minutes. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, and extracted three times 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 recrystallized from diisopropyl ether-hexane to obtain 1.95 g of the title compound.

Workup

  1. temperaturewith cooling on ice
  2. stirringstirred at room temperature for 30 minutes and at 60° C. for 15 minutes
  3. extractionextracted three times with ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-0cb68535f2ce41889ee67787207719b6
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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