تفاعل #546688

معادلة التفاعل

(1R*,4R*,5R*)-4-Iodo-6-oxabicyclo [3.2.1]octan-7-one

ethanol

sodium hydroxide

→

title compound

Ethyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate

ظروف التفاعل

المعالجة

1. 1
   workup.DISTILLATIONAfter the solvent was distilled off under reduced pressure, and water
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   استخلاصextraction with dichloromethane
4. 4
   تجفيفthe extract was dried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
6. 6
   أخرىthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17)

الإجراء التجريبي

(1R*,4R*,5R*)-4-Iodo-6-oxabicyclo [3.2.1]octan-7-one (J. Org. Chem., 1996, Vol. 61, p. 8687) (14.3 g) was dissolved in ethanol (130 ml), a 2N aqueous solution (34.5 ml) of sodium hydroxide was added under ice cooling, and the mixture was then stirred at room temperature for 7 hours. After the solvent was distilled off under reduced pressure, and water was added to the residue to conduct extraction with dichloromethane, the extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17) to obtain the title compound (6.54 g) as a colorless oil.

المصدر