تفاعل #633637

معادلة التفاعل

ethanol

(1S,4S,5S)-4-Iodo-6-oxabicyclo[3.2.1]octan-7-on

sodium hydroxide

→

title compound

Ethyl (1S,3S,4R)-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 magnesium 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=17:3)

الإجراء التجريبي

(1S,4S,5S)-4-Iodo-6-oxabicyclo[3.2.1]octan-7-on (J. Org. Chem., 1996, Vol. 61, p. 8687) (89.3 g) was dissolved in ethanol (810 ml), a 2N aqueous solution (213 ml) of sodium hydroxide was added, and the mixture was then stirred at room temperature for 3 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 magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=17:3) to obtain the title compound (41.2 g) as a pale yellow oil.

المصدر