Réaction #1772061

ord-b86ec42eca8e44ee86f800293e15d7e3

Équation de réaction

C=Cc1ccc(O)cc1
4-Hydroxy styrene
NC(N)=O.OO
urea hydrogen peroxide
CC1(C)OC[C@@H]2O[C@@]3(C(=O)O)OC(C)(C)O[C@H]3[C@@H]2O1.O
2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid monohydrate
→
Oc1ccc(C2CO2)cc1
4-hydroxyphenyloxirane
Rendement 66.0%

Réactifs

C=Cc1ccc(O)cc1
4-Hydroxy styrene
NC(N)=O.OO
urea hydrogen peroxide
CC1(C)OC[C@@H]2O[C@@]3(C(=O)O)OC(C)(C)O[C@H]3[C@@H]2O1.O
2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid monohydrate

Réactifs

Aucun

Solvants

C1CCOC1.ClCCl
dichloromethane tetrahydrofuran

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreReaction time
  2. 2
    Autre20 hours, Yield: 66%

Mode opératoire

Fifth recycle 4-Hydroxy styrene: 1 g, 8.3 mmol, urea hydrogen peroxide: 3 g, 32 mmol, Immobilized lipase: 87 mg, 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid monohydrate: 0.3 g, 1.03 mmol, dry dichloromethane:tetrahydrofuran (4:1): 15 mL. Same procedure was followed as described in example ‘1’. Reaction time: 20 hours, Yield: 66%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08148118B2uspto-grants-2012_04