Reaction #312338

Reaction equation

hydrogen peroxide

hydrogen peroxide

1-phenyl-2-cyano-2-(ethoxycarbonyl)-1,2-epoxyethane

methanol

tribasic sodium phosphate

→

Methyl 2-(aminocarbonyl)-3-phenyloxiranecarboxylate

Solvents

ether

Conditions

Workup

1. 1
   workup.ADDITIONto rise to 50° C. during the addition
2. 2
   Otherrose to 48° C
3. 3
   Temperaturewas raised to 60° C.
4. 4
   workup.WAITheld there for 2 hours
5. 5
   OtherThe volatile materials were evaporated under reduced pressure
6. 6
   OtherThe residue was recrystallized from chloroform
7. 7
   Otherto give 8, mp: 175°-177° C.

Procedure

100 ml of 30% hydrogen peroxide was added over a 20-minute period to a stirred mixture of 67 g of 1-phenyl-2-cyano-2-(ethoxycarbonyl)-1,2-epoxyethane (Reference II), 400 ml of methanol, 20 g of tribasic sodium phosphate (hydrate) and 8 g of 18 crown 6 ether at 25° C. The temperature was allowed to rise to 50° C. during the addition. The mixture then was cooled to 45° C. and 150 ml of the hydrogen peroxide solution was added over a 10-minute period. The temperature rose to 48° C. It was held there for one hour, then was raised to 60° C. and held there for 2 hours. The volatile materials were evaporated under reduced pressure. The residue was recrystallized from chloroform to give 8, mp: 175°-177° C.

Source