Reaktion #64056

Reaktionsgleichung

Iodotrimethylsilane

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

→

2-butyryl-5-(3-ethoxymethyl-2,4,6-trimethylphenyl)-3-hydroxycyclohex-2-en-1-one

Ausbeute 84.7%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated
2. 2
   workup.STIRRINGthe residue was stirred with an ethanolic potassium hydroxide solution at room temperature for 15 hours
3. 3
   workup.ADDITIONThe solution was poured into dilute hydrochloric acid
4. 4
   Extraktionextracted with diethyl ether
5. 5
   ExtraktionThe ether extract
6. 6
   Trocknenwas dried over anhydrous magnesium sulfate
7. 7
   Sonstigeevaporated under reduced pressure
8. 8
   SonstigePurification by column chromatography over silica gel (eluant dichloromethane)

Vorschrift

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.

Quelle