Reaktion #64057

Reaktionsgleichung

Iodotrimethylsilane

2-butyryl-3-hydroxy-5-(3-methoxymethyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one

→

2-butyryl-3-hydroxy-5-(3-hydroxymethyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one

Ausbeute 87.7%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for a further 4 hours
2. 2
   SonstigeThe solvent was evaporated
3. 3
   Waschenthe residue was washed successively with dilute aqueous sodium hydroxide and acetic acid
4. 4
   workup.DISSOLUTIONdissolved in ethyl acetate
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   SonstigeEvaporation under reduced pressure

Vorschrift

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.

Quelle