Magnesium monoxide → HCID 19080720, compound

HRID 234596Notes

Reaction equation

HRID 234596 reaction equation
Cl[C:2]1[C:7]([CH:8]([C:10]2[C:11](Cl)=[N:12][CH:13]=[CH:14][C:15]=2[C:16]([F:19])([F:18])[F:17])[OH:9])=[C:6]([C:21]([F:24])([F:23])[F:22])[CH:5]=[CH:4][N:3]=1.[O-2].[Mg+2].[H][H]>CO.[Pd].C(Cl)Cl>[F:19][C:16]([F:17])([F:18])[C:15]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[CH:8]([C:7]1[CH:2]=[N:3][CH:4]=[CH:5][C:6]=1[C:21]([F:22])([F:24])[F:23])[OH:9]

Participants

7

Reactant 3

HCID 6850729Magnesium monoxideHCID 19080717HCID 19080717, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19080720HCID 19080720, compoundYield 80.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.4 g of 1,1-bis-(2-chloro-4-trifluoromethylpyrid-3-yl)methanol in 12 ml of methanol were added 0.8 g of magnesium oxide and 0.3 g of 5% palladium on carbon. This mixture was then shaken on a Parr hydrogenation apparatus overnight under 50 psi of hydrogen. The palladium catalyst and magnesium oxide were removed via filtration through dicalite, and the methanol filtrate was concentrated in vacuo to afford 1.6 of a yellow solid. This solid was dissolved in 25 ml of methylene chloride. The methylene chloride solution was washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 0.93 g of 1,1-bis-(4-trifluoromethylpyrid-3-yl)methanol as a yellow solid.

Workup

  1. customThe palladium catalyst and magnesium oxide were removed via filtration through dicalite
  2. concentrationthe methanol filtrate was concentrated in vacuo
  3. customto afford 1.6 of a yellow solid
  4. washThe methylene chloride solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4b6b6f9d52b46b0929bf22ed13d3921
Source dataset
uspto-grants-1997_01
Patent number
US05595958

Reaction notes

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