2,6-Di-tert-butyl-4-methylphenol → HCID 15239537, compound

HRID 1609448Notes

Reaction equation

HRID 1609448 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:26]=[CH:25][CH:24]=[C:23](OS(C(F)(F)F)(=O)=O)[C:13]=2[C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])[N:4]=1.[C:35](C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)[CH3:36].C([Sn](CCCC)(CCCC)CCCC)=C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[CH:26]=[CH:25][CH:24]=[C:23]([CH:35]=[CH2:36])[C:13]=2[C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:22])[CH3:21])=[O:15])[N:6]=1

Participants

6

Reactant 3

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 81998TributylvinyltinHCID 15239536HCID 15239536, compound

Product 1

HCID 15239537HCID 15239537, compoundYield 20.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Procedure

In a 100 ml flask equipped with a thermometer, a cooling tube and a nitrogen-introducing tube, there were charged 2-trimethylsilylethyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-trifluoromethylsulfonyloxybenzoate (3.15 g, 6.0 mmol), tetrakis(triphenylphosphine)palladium(0) (400 mg, 0.34 mmol) and toluene (30 ml), and the resultant mixture was stirred at room temperature for 1 hour under nitrogen stream. After adding 2,6-di-tert-butyl-4-methylphenol (catalytic amount) to the resultant mixture, vinyl tributyl tin (3.17 g, 10.0 mmol) was further added and the mixture was reacted at 80°-90° C. for 3 hours. After cooling the mixture, toluene was added thereto and the organic layer was washed with water and a saturated salt water, dried with anhydrous sodium sulfate and concentrated. The residue thus obtained was purified by silica gel column chromatography to obtain 0.50 g (yield: 20.8%) of the aimed product (transparent viscous orange color liquid).

Workup

  1. customIn a 100 ml flask equipped with a thermometer, a cooling tube
  2. additiona nitrogen-introducing tube
  3. additionwas further added
  4. customthe mixture was reacted at 80°-90° C. for 3 hours
  5. additionwas added
  6. washthe organic layer was washed with water
  7. dry with materiala saturated salt water, dried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue thus obtained
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5a2b7148572645f7b28b642b75c22e6d
Source dataset
uspto-grants-1995_03
Patent number
US05401711

Reaction notes

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