Reaktion #468412

Reaktionsgleichung

Methyl (S)-(+)-3-hydroxybutyrate

benzyl 2,2,2-trichloroacetimidate

trifluoromethane sulfonic acid

→

Methyl (S)-3-benzyloxybutyrate

Lösungsmittel

cyclohexane methylene chloride

cyclohexane methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   WaschenThe organic layer was washed with 50 mL of saturated sodium bicarbonate and 50 mL of distilled water
3. 3
   TrocknenAfter drying with anhydrous sodium sulfate the solution
4. 4
   Filtrationwas filtered
5. 5
   Sonstigethe solvents were removed on a rotovap
6. 6
   SonstigeThe resulting solid was purified
7. 7
   Waschensilica gel and elution with ether/hexane (1:4)

Vorschrift

Methyl (S)-(+)-3-hydroxybutyrate (17) (2.223 g, 18.82 mmol) and benzyl 2,2,2-trichloroacetimidate (4.2 mL) were dissolved into 37.5 mL of cyclohexane/methylene chloride (2:1). After the addition of 0.2 mL of trifluoromethane sulfonic acid the reaction was stirred under nitrogen for one hour. The reaction was diluted with 75 mL of cyclohexane/methylene chloride (2:1) and filtered. The organic layer was washed with 50 mL of saturated sodium bicarbonate and 50 mL of distilled water. After drying with anhydrous sodium sulfate the solution was filtered and the solvents were removed on a rotovap. The resulting solid was purified using silica gel and elution with ether/hexane (1:4).

Quelle