Sodium hydride → HCID 12056886, compound

HRID 842568Notes

Reaction equation

HRID 842568 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[C:9]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][OH:8].[H-].[Na+].Cl[C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=1>CN(C)C=O>[CH2:14]([O:13][C:11]1[CH:12]=[C:2]([Cl:1])[C:3]([O:4][CH2:5][CH2:6][CH2:7][O:8][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=2)=[C:9]([Cl:21])[CH:10]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 120568873-(2,6dichloro-4-(benzyloxy)phenoxy)-1-propyl alcohol

Product 1

HCID 12056886HCID 12056886, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.5 g of 3-(2,6-dichloro-4-(benzyloxy)phenoxy)-1-propyl alcohol thus obtained, 0.1 g of an oily mixture containing 60% sodium hydride, and 3 ml of N,N-dimethylformamide was stirred at room temperature for 1 hour. Then, 0.3 g of 2-chloro-5-trifluoromethylpyridine was added to this mixture, followed by heating to 100° C. After stirring continued for 1 hour, the mixture was poured into 50 m of ice-water, and extracted with toluene at a total volume of 50 ml. The combined toluene layer was successively washed with diluted hydrochloric acid and aqueous sodium bicarbonate solution, dried with magnesium sulfate, and concentrated. The residue was silica gel chromatography, which afforded 0.5 g of 1-benzyloxy-3,5-dichloro-4-[3-(5-trifluoromethylpyridin-2-yloxy)propyloxy]benzene (67% yield).

Workup

  1. customthus obtained
  2. temperatureby heating to 100° C
  3. stirringAfter stirring
  4. waitcontinued for 1 hour
  5. extractionextracted with toluene at a total volume of 50 ml
  6. washThe combined toluene layer was successively washed with diluted hydrochloric acid and aqueous sodium bicarbonate solution
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4dd43bc81c694c9f8784c3b5f78e3c27
Source dataset
uspto-grants-2002_04
Patent number
US06376428B1

Reaction notes

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