Trimethylsilyl iodide → HCID 178450319, compound

HRID 35779Notes

Reaction equation

HRID 35779 reaction equation
I[Si](C)(C)C.[C:6]([C:11]1[C:12](=[O:30])[CH2:13][CH:14]([C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[C:20]([CH2:26][O:27]C)[C:19]=2[CH3:29])[CH2:15][C:16]=1[OH:17])(=[O:10])[CH2:7][CH2:8][CH3:9]>C(#N)C.[N+]([O-])([O-])=O.[Ag+]>[C:6]([C:11]1[C:16](=[O:17])[CH2:15][CH:14]([C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[C:20]([CH2:26][OH:27])[C:19]=2[CH3:29])[CH2:13][C:12]=1[OH:30])(=[O:10])[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 178450320HCID 178450320, compound

Product 1

HCID 178450319HCID 178450319, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6342AcetonitrileSolvent

Procedure

Iodotrimethylsilane (0.3 ml) was added to a solution of 2-butyryl-3-hydroxy-5-(3-methoxymethyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (0.5 g, 1.45 mmole) (see Example 36) in dry acetonitrile (10 ml) under nitrogen and the mixture was stirred at room temperature for 15 minutes. An aqueous solution of silver nitrate was added and the mixture was stirred for a further 4 hours. The solvent was evaporated and the residue was washed successively with dilute aqueous sodium hydroxide and acetic acid, then dissolved in ethyl acetate and dried over anhydrous sodium sulfate. Evaporation under reduced pressure yielded 2-butyryl-3-hydroxy-5-(3-hydroxymethyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (0.42 g; 87.0%) as an oil.

Workup

  1. stirringthe mixture was stirred for a further 4 hours
  2. customThe solvent was evaporated
  3. washthe residue was washed successively with dilute aqueous sodium hydroxide and acetic acid
  4. dissolutiondissolved in ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-a3782001c16943e0ad4169429c50de1b
Source dataset
uspto-grants-1988_08
Patent number
US04767879

Reaction notes

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