Methyl iodide → HCID 18973417, compound

HRID 2394450Notes

Reaction equation

HRID 2394450 reaction equation
[OH:1][CH:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][N:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:13]([OH:15])=[O:14])[C:7]=2[CH:6]=[CH:5]1.CI.[C:24](=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[OH:1][CH:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][N:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:13]([O:15][CH3:24])=[O:14])[C:7]=2[CH:6]=[CH:5]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 189733641-(2-Hydroxy-2-phenylethyl)-1H-indole-4-carboxylic acid

Product 1

HCID 18973417HCID 18973417, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

There were dissolved, in 80 ml of dimethylformamide, 5.39 g of 1-(2-hydroxy-2-phenylethyl)indole-4-carboxylic acid prepared in Example 319 and 3.05 g of methyl iodide, followed by further addition of 2.91 g of potassium carbonate and stirring at room temperature for 30 minutes. The reaction system was poured into 300 ml of a 10% ammonium chloride aqueous solution and extracted with ethyl acetate (100 ml×3). The resulting organic phase was washed, in order, with a 10% citric acid aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give 5.14 g of methyl 1-(2-hydroxy-2-phenylethyl)indole-4-carboxylate as a yellow oily substance. The yield thereof was found to be 91%.

Workup

  1. extractionextracted with ethyl acetate (100 ml×3)
  2. washThe resulting organic phase was washed, in order, with a 10% citric acid aqueous solution
  3. dry with materiala saturated common salt solution, dried over anhydrous sodium sulfate
  4. customthe solvent was removed by evaporation under reduced pressure
  5. customto give a crude product
  6. customThe crude product was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-2aff65a209cb4b70ac8836314b196af0
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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