Trimethylsilyl iodide → HCID 178450321, compound

HRID 978993Notes

Reaction equation

HRID 978993 reaction equation
I[Si](C)(C)[CH3:3].[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][CH3:28])[C:19]=2[CH3:29])[CH2:15][C:16]=1[OH:17])(=[O:10])[CH2:7][CH2:8][CH3:9]>C(#N)C>[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][O:27][CH2:28][CH3:3])[C:19]=2[CH3:29])[CH2:13][C:12]=1[OH:30])(=[O:10])[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 178450320HCID 178450320, compound

Product 1

HCID 178450321HCID 178450321, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Iodotrimethylsilane (0.5 ml) was added to a solution of 2-butyryl-3-hydroxy-5-(3-methoxymethyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (1.50 g; 4.36 mmole) (see Example 36) in dry acetonitrile (10 ml) under nitrogen and the mixture was stirred at room temperature for 15 minutes. The solvent was evaporated and the residue was stirred with an ethanolic potassium hydroxide solution at room temperature for 15 hours. The solution was poured into dilute hydrochloric acid and then extracted with diethyl ether. The ether extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. Purification by column chromatography over silica gel (eluant dichloromethane) gave 2-butyryl-5-(3-ethoxymethyl-2,4,6-trimethylphenyl)-3-hydroxycyclohex-2-en-1-one (1.32 g; 84.7%) as an oil.

Workup

  1. customThe solvent was evaporated
  2. stirringthe residue was stirred with an ethanolic potassium hydroxide solution at room temperature for 15 hours
  3. additionThe solution was poured into dilute hydrochloric acid
  4. extractionextracted with diethyl ether
  5. extractionThe ether extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customPurification by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-b2dc83bd724d4414890463d27c224ea4
Source dataset
uspto-grants-1987_05
Patent number
US04666510

Reaction notes

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