Potassium Carbonate → Pyridalyl

HRID 1356965Notes

Reaction equation

HRID 1356965 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:24])[CH:5]=[C:6]([Cl:23])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=1.[Cl:25][C:26]([Cl:30])=[CH:27][CH2:28]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:24][CH2:28][CH:27]=[C:26]([Cl:30])[Cl:25])[CH:5]=[C:6]([Cl:23])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 185045573,5-Dichloro-4-[3-[[5-(trifluoromethyl)-2-pyridinyl]oxy]propoxy]phenol

Product 1

HCID 11488729PyridalylYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.5 g of 3,5-dichloro-4-[3-(5-trifluoromethylpyridin-2-yloxy)propyloxy]phenol, 0.25 g of 1,1,3-trichloropropene, 0.2.g of potassium carbonate and 3 ml of N,N-dimethylformamide was stirred at room temperature overnight. The reaction mixture was subjected to silica gel chromatography, which afforded 0.3 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridin-2-yloxy)propyloxy]benzene (47% yield), nD20.5 1.5377.

Sources & evidence

ORD record
ord-a3e695bf037f405ab287eabd154b8af1
Source dataset
uspto-grants-2003_07
Patent number
US06589914B2

Reaction notes

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