Water → HCID 86659403, compound

HRID 1187731Notes

Reaction equation

HRID 1187731 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].[Cl:8][C:9]1[CH:14]=[C:13](Cl)[CH:12]=[C:11]([Cl:16])[N:10]=1.O>CN(C)C=O>[Cl:8][C:9]1[CH:14]=[C:13]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[CH:12]=[C:11]([Cl:16])[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27665Pyridine, 2,4,6-trichloro-HCID 75644Cyclopropanemethanol

Product 1

HCID 86659403HCID 86659403, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

109 mg of cyclopropylcarbinol was dissolved in 2 ml of dimethylformamide, and 60 mg of 60% sodium hydride was added thereto under ice water cooling, and the mixture was stirred at room temperature for 20 minutes. To the reaction solution was added 400 mg of 2,4,6-trichloropyridine, and stirred at room temperature for 30 minutes. The reaction solution was added with water and subjected to extraction with ethyl acetate. The organic layer was washed with brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 133 mg of the objective compound as colorless oil.

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-35c0577cdf31419995c3a8e8093124af
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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