Reaktion #1106426

Reaktionsgleichung

(6R/S,9R)6-Methyl-9-(1-methylvinyl)-bicyclo[4.4.0]dec-1-ene-3-one

sulfuric acid

K2CO3

→

product

Ausbeute 39.0%

(6R/S,9R)6-Methyl-9-(1-hydroxyisopropyl)-bicyclo[4.4.0]dec-1-ene-3-one

Ausbeute 39.0%

Lösungsmittel

formic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith cooling
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe extract was washed with saturated NaHCO3 solution and brine
4. 4
   Sonstigedried
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 5/1)

Vorschrift

1.2 g (5.87 mmol) of (6R/S,9R)6-Methyl-9-(1-methylvinyl)-bicyclo[4.4.0]dec-1-ene-3-one from step C of preparation A was dissolved in 20 mL of formic acid and added to 4 mL of 5% sulfuric acid solution. The reaction mixture was stirred at room temperature for 2 days, in refrigerator for 3 days, then neutralized with K2CO3 with cooling, and extracted with ethyl acetate. The extract was washed with saturated NaHCO3 solution and brine, dried, and evaporated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 5/1) to give 500 mg of product as oil and 620 mg of recovered starting material, yield 39%.

Quelle