Methyl iodide → Methyl α-propoxy-1H-indole-5-propanoate

HRID 2181192Notes

Reaction equation

HRID 2181192 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH:11]([O:15][CH2:16][CH2:17][CH3:18])[C:12]([OH:14])=[O:13])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:19](=O)([O-])O.[Na+].CI>CN(C)C=O>[CH3:19][O:13][C:12](=[O:14])[CH:11]([O:15][CH2:16][CH2:17][CH3:18])[CH2:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 22485685HCID 22485685, compound

Product 1

HCID 69562937Methyl α-propoxy-1H-indole-5-propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude rac-3-(1H-indol-5-yl)-2-propoxy-propionic acid was dissolved in 5 ml N,N-dimethylformamide, 0.54 g of sodium hydrogencarbonate was added followed by 0.32 nm of methyl iodide. The mixture was stirred at r.t. for 7 hours, then poured into ice water and extracted 3 times with ethyl acetate; after drying over MgSO4 and evaporation, the crude product was purified by chromatograph) (silicagel, eluent: gradient of n-heptane/ethyl acetate) to yield 0.47 g of rac-3-(1H-indol-5-yl)-2-propoxy-propionic acid methyl ester as light yellow oil.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. dry with materialafter drying over MgSO4 and evaporation
  3. customthe crude product was purified by chromatograph) (silicagel, eluent: gradient of n-heptane/ethyl acetate)

Sources & evidence

ORD record
ord-7aac6d65b86b47ac843f7eada6c2ab1f
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

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