Water → 1-{[(2,2-Dimethylpropanoyl)oxy]methyl}-1H-indole-3-carboxylic acid

HRID 1393669Notes

Reaction equation

HRID 1393669 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4]1.Cl[CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20].O>CN(C)C=O>[CH3:20][C:19]([CH3:22])([CH3:21])[C:18]([O:17][CH2:16][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4]1)=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 69867Indole-3-Carboxylic AcidHCID 87885Chloromethyl pivalate

Product 1

HCID 230919581-{[(2,2-Dimethylpropanoyl)oxy]methyl}-1H-indole-3-carboxylic acidYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (218 mg) was added to a solution of 1H-indole-3-carboxylic acid (400 mg) in N,N-dimethylformamide (4 ml) with ice cooling, and the mixture was stirred for 30 minutes. Chloromethyl2,2-dimethylpropionate (373 mg) was added thereto, and the mixture was warmed to room temperature and stirred for 2 hours. Water was added thereto, and the aqueous phase was washed with ether. The aqueous phase was acidified by 2 N hydrochloric acid and extracted with ether. The organic phase was washed with a saturated saline solution and dried over sodium sulfate anhydrous. The product was concentrated under reduced pressure to give the title compound (540 mg, Y.:79%) as orange crystals.

Workup

  1. stirringstirred for 2 hours
  2. washthe aqueous phase was washed with ether
  3. extractionextracted with ether
  4. washThe organic phase was washed with a saturated saline solution
  5. dry with materialdried over sodium sulfate anhydrous
  6. concentrationThe product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4535099975ed4cd5a5e4326e7213b2b9
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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