Potassium Carbonate → HCID 15869647, compound

HRID 582334Notes

Reaction equation

HRID 582334 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:26])[CH:6]=[C:7]([CH2:24][CH3:25])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:33][C:34]([Cl:38])=[CH:35][CH2:36]Cl>CN(C)C=O>[CH2:24]([C:7]1[CH:6]=[C:5]([O:26][CH2:36][CH:35]=[C:34]([Cl:38])[Cl:33])[CH:4]=[C:3]([CH2:1][CH3:2])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:16][N:15]=1)[CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 15869646HCID 15869646, compound

Product 1

HCID 15869647HCID 15869647, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 10 ml of N,N-dimethylformamide were dissolved 0.45 g of 3,5-diethyl-4-[3-(5-trifluoromethyl-2-pyridyloxy)propyloxy]phenol and 0.17 g of potassium carbonate, to which a solution of 0.18 g of 1,1,3-trichloropropene dissolved in 5 ml of N,N-dimethylformamide was added dropwise, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was poured into ice-water, and extracted twice with 100 ml of diethyl ether. The combined diethyl ether was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude produce was subjected to silica gel chromatography, which afforded 0.35 g of 3,5-diethyl-4-[3-(5-trifluoromethyl-2-pyridyloxy)propyloxy]-1-(3,3-dichloro-2-propenyloxy)benzene (60% yield), nD20.0 1.5192.

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring at room temperature for 12 hours
  3. extractionextracted twice with 100 ml of diethyl ether
  4. washThe combined diethyl ether was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto obtain a crude product
  8. customThe crude produce

Sources & evidence

ORD record
ord-62808a8ba6aa498daf851ad9558fcea2
Source dataset
uspto-grants-1999_07
Patent number
US05922880

Reaction notes

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