Sodium Hydroxide → 1-Acetyl-3-(2-hydroxyethyl)-4,6-dimethylindoline

HRID 1107955Notes

Reaction equation

HRID 1107955 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[C:10]([CH3:13])[CH:11]=2)[CH:6]([CH2:15][CH2:16][O:17]C(=O)C)[CH2:5]1)(=[O:3])[CH3:2].[OH-].[Na+]>C(Cl)(Cl)Cl.CO.O>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[C:10]([CH3:13])[CH:11]=2)[CH:6]([CH2:15][CH2:16][OH:17])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 222473471-Acetyl-3-(2-acetoxyethyl)-4,6-dimethylindoline

Product 1

HCID 222473161-Acetyl-3-(2-hydroxyethyl)-4,6-dimethylindolineYield 70.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21584188Chloroform methanolSolvent

Procedure

1-Acetyl-3-(2-acetoxyethyl)-4,6-dimethylindoline (2.0 g) was dissolved in a mixture of CHCl3 /MeOH=1/1 (25 ml), and a solution of NaOH (1.5 g) in water (5 ml) was added, which was followed by stirring at room temperature for 1 hr. The solvent was evaporated under reduced pressure. CHCl3 (100 ml) was added, and the mixture was washed with water and dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1) to give 1.2 g of 1-acetyl-3-(2-hydroxyethyl)-4,6-dimethylindoline.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionCHCl3 (100 ml) was added
  3. washthe mixture was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customCHCl3 was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1)

Sources & evidence

ORD record
ord-f1bb1c3f82d44a7bab3e1d893d7f0ea0
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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