Acetic Acid → HCID 14343503, compound

HRID 2351111Notes

Reaction equation

HRID 2351111 reaction equation
[F-].[K+].[C:3]([C:7]1[C:8](=[O:18])[C:9](=[O:17])[CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)([CH3:6])([CH3:5])[CH3:4].C(O)(=O)C.C([Si](CC)(CC)[C:26]([F:29])([F:28])[F:27])C>C(#N)C>[C:13]([C:11]1[CH:12]=[C:7]([C:3]([CH3:6])([CH3:4])[CH3:5])[C:8](=[O:18])[C:9]([OH:17])([C:26]([F:29])([F:28])[F:27])[CH:10]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 769153,5-Di-tert-butyl-1,2-benzoquinoneHCID 522689Potassium FluorideHCID 4204914Triethyl(trifluoromethyl)silane

Product 1

HCID 14343503HCID 14343503, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 100 mg (1.7 mmol) of potassium fluoride, 132 mg (0.60 mmol) of 3,5-di-tert-butyl-1,2-benzoquinone, and 2 mL of acetonitrile was treated successively with 40 μL (0.70 mmol) of glacal acetic acid and 129 mg (0.70 mmol) of triethyltrifloromethylsilane, and stirred vigorously at room temperature for 15 minutes. The mixture was filtered and the filter cake was washed with dichloromethane. Concentration of the combined filtrates afforded a residue which was purified by PTLC (one 2 mm silica gel plate eluted with 20% dichloromethane--80% petroleum ether) to give 27 mg (16% yield) of 4,6-di-tert-butyl-2-hydroxy-2-trifluoromethyl-3,5-cyclohexadiene-one.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with dichloromethane
  3. customConcentration of the combined filtrates afforded a residue which
  4. customwas purified by PTLC (one 2 mm silica gel plate eluted with 20% dichloromethane--80% petroleum ether)

Sources & evidence

ORD record
ord-2868d2cb5dc94f70b71145d21e873a49
Source dataset
uspto-grants-1989_10
Patent number
US04871877

Reaction notes

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