تفاعل #633642

معادلة التفاعل

sodium thiosulfate

Benzyl (±)-3-cyclohexene-1-carboxylate

m-chloroperbenzoic acid

→

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

title compound

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

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGto conduct stirring for 20 minutes
2. 2
   أخرىan organic layer was separated
3. 3
   غسيلwashed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline
4. 4
   تجفيفdried 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 (ethyl acetate:hexane=1:9)

الإجراء التجريبي

Benzyl (±)-3-cyclohexene-1-carboxylate (40 g) was dissolved in dichloromethane (500 ml), and m-chloroperbenzoic acid (86 g) was added under ice cooling to stir the mixture for 2 hours. After a 10% aqueous solution of sodium thiosulfate was added to conduct stirring for 20 minutes, an organic layer was separated, washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9) to obtain the title compound (23.4 g) and benzyl (1R,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (12.1 g) as colorless oils.

المصدر