Hydrochloric Acid → HCID 59201058, compound

HRID 1690156Notes

Reaction equation

HRID 1690156 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:24][CH2:25][O:26][CH3:27])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[CH2:28][CH2:29][CH3:30])[CH:5]=[CH:4][N:3]=1.O.Cl.O1CCOC[CH2:34]1>CCCCCCC.C[Al](C)C>[F:17][C:16]([F:19])([F:18])[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:34])[CH:7]=2)=[C:10]([CH2:28][CH2:29][CH3:30])[CH:11]=1)([O:24][CH2:25][O:26][CH3:27])[C:20]([F:23])([F:22])[F:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 312751,4-DioxaneHCID 59201016HCID 59201016, compound

Product 1

HCID 59201058HCID 59201058, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 19878572HCID 19878572, compoundSolvent

Procedure

To a solution of 2-chloro-4-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy) pyridine (867 mg, 559 μmol) in 1,4-dioxane, trimethylaluminum heptane solution (2 mol/L, 1.13 mL) and tetrakis triphenylphosphine palladium complex (218 mg) were added at room temperature under an argon atmosphere, and then the resultant mixture was heated at 80° C. After completion of the reaction, the reaction solution was neutralized by adding water and 2 mol/L of hydrochloric acid, extracted with ethyl acetate, and then concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and the title compound (780 mg, yield 94%) was obtained as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo
  4. customThe obtained residue was purified

Sources & evidence

ORD record
ord-f371e6c40a7c4c31a725da5f0047325f
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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