2,6-Di-tert-butyl-4-methylphenol → HCID 15279415, compound

HRID 1779318Notes

Reaction equation

HRID 1779318 reaction equation
[CH3:1][C:2]1([CH3:21])[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11](OS(C(F)(F)F)(=O)=O)[C:5]=2[C:4](=[O:20])[O:3]1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([Sn](CCCC)(CCCC)CCCC)=[CH:26][N:25]=1.[Cl-].[Li+].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>O1CCOCC1>[CH3:1][C:2]1([CH3:21])[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([C:27]3[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[N:25][CH:26]=3)[C:5]=2[C:4](=[O:20])[O:3]1

Participants

6

Reactant 4

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 433294Lithium ChlorideHCID 108927482,2-Dimethyl-4-oxo-4H-benzo[D][1,3]dioxin-5-YL trifluoromethanesulfonateHCID 117290212-Methoxy-5-(tributylstannyl)pyridine

Product 1

HCID 15279415HCID 15279415, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

8.7 g of 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one, 23.2 g of 2-methoxy-5-tributylstannylpyridine, 3.4 g of lithium chloride, 0.6 g of tetrakistriphenylphosphinepalladium0 and 70 mg of 2,6-di-t-butyl-4-methylphenol are dissolved in 150 ml of dioxane and the mixture is stirred for 3 h at 140° C. in an autoclave. It is then concentrated under reduced pressure, the residue is stirred with 200 ml of n-pentane and filtered on a little silica gel 60, the latter is subsequently washed with n-pentane and the product is eluted using ethyl acetate. After concentration, 10.3 g of m.p. 160° C. remain.

Workup

  1. concentrationIt is then concentrated under reduced pressure
  2. stirringthe residue is stirred with 200 ml of n-pentane
  3. filtrationfiltered on a little silica gel 60
  4. washthe latter is subsequently washed with n-pentane
  5. washthe product is eluted
  6. concentrationAfter concentration, 10.3 g of m.p. 160° C.

Sources & evidence

ORD record
ord-7413032d1f20446ebe71f8f490a5d3a2
Source dataset
uspto-grants-1997_05
Patent number
US05627136

Reaction notes

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