Potassium Carbonate → HCID 18504655, compound

HRID 1420496Notes

Reaction equation

HRID 1420496 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:26])[CH:6]=[C:7]([CH3:25])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:33][C:34]([Cl:38])=[CH:35][CH2:36]Cl>CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[C:5]([O:26][CH2:36][CH:35]=[C:34]([Cl:38])[Cl:33])[CH:6]=[C:7]([CH3:25])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][N:16]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 18504607HCID 18504607, compound

Product 1

HCID 18504655HCID 18504655, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 10 ml of N,N-dimethylformamide were dissolved 0.6 g of 3-ethyl-5methyl-4-[4-(5-trifluoromethyl-2-pyridyloxy)butyloxy]phenol and 0.23 g of potassium carbonate, to which a solution of 0.28 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 0.50 g of 3-ethyl-5-methyl-4-[4-(5-trifluoromethyl-2-pyridyloxy)butyloxy]-1-(3,3-dichloro-2-propenyloxy)benzene (64% yield), nD23.0 1.5170.

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-01007b120b414f6095d4a7efa8ff6413
Source dataset
uspto-grants-2000_06
Patent number
US06071861

Reaction notes

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