Sodium Chloride → 1-[3-(4-Heptyloxyphenoxy)-2-hydroxypropyl]indole-5-carbonitrile

HRID 1821957Notes

Reaction equation

HRID 1821957 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[O:18]1[CH2:20][CH:19]1[CH2:21][N:22]1[C:30]2[C:25](=[CH:26][C:27]([C:31]#[N:32])=[CH:28][CH:29]=2)[CH:24]=[CH:23]1.[Na+].[Cl-]>CN(C=O)C>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:20][CH:19]([OH:18])[CH2:21][N:22]2[C:30]3[C:25](=[CH:26][C:27]([C:31]#[N:32])=[CH:28][CH:29]=3)[CH:24]=[CH:23]2)=[CH:13][CH:12]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 256414-(Heptyloxy)phenolHCID 468686361-Oxiranylmethylindole-5-carbonitrile

Product 1

HCID 578938361-[3-(4-Heptyloxyphenoxy)-2-hydroxypropyl]indole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

0.13 g (2.47 mmol) sodium hydride as 60% dispersion in mineral oil is suspended in 10 ml absolute DMF under nitrogen, stirred at room temperature for 10 min and mixed with the solution of 0.5 g (2.39 mmol) 4-heptyloxyphenol in 5 ml absolute DMF. Having stirred for 1 hour, a solution of 475 mg (2.39 mmol) 1-oxiranylmethylindole-5-carbonitrile in 5 ml absolute DMF is added and stirring is continued at room temperature overnight. Thereafter, the suspension is hydrolyzed with semi-saturated NaCl solution and extracted three times with ethyl acetate. The extracts are washed with saturated NaCl solution, dried on sodium sulfate and the solvent is distilled off. The residue is purified on silica gel by means of column chromatography (flow agent: hexane/ethyl acetate 1:1), the product accruing as an oil.

Workup

  1. stirringHaving stirred for 1 hour
  2. stirringstirring
  3. waitis continued at room temperature overnight
  4. extractionextracted three times with ethyl acetate
  5. washThe extracts are washed with saturated NaCl solution
  6. customdried on sodium sulfate
  7. distillationthe solvent is distilled off
  8. customThe residue is purified on silica gel by means of column chromatography (flow agent: hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-10336817693b4cbfb1f624cf933561e8
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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