Reaktion #1005563

ord-66d6ed8a770344c49352832daf0e35bf

Reaktionsgleichung

C=C(CO[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CCl)c1ccccc1
21-chloro-9-fluoro-11β,17-dihydroxy-16α-[(2-phenyl-2-propenyl)oxy]pregna-1,4-diene-3,20-dione
O=C(OO)c1cccc(Cl)c1
m-chloroperbenzoic acid
→
C[C@]12C=CC(=O)C=C1CC[C@H]1[C@@H]3C[C@@H](OCC4(c5ccccc5)CO4)[C@](O)(C(=O)CCl)[C@@]3(C)C[C@H](O)[C@@]12F
21-chloro-9-fluoro-11β,17-dihydroxy-16α-[(2-phenyloxiranyl)methoxy]pregna-1,4-diene-3,20-dione
Ausbeute 116.5%

Edukte

C=C(CO[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CCl)c1ccccc1
21-chloro-9-fluoro-11β,17-dihydroxy-16α-[(2-phenyl-2-propenyl)oxy]pregna-1,4-diene-3,20-dione
O=C(OO)c1cccc(Cl)c1
m-chloroperbenzoic acid

Reagenzien

Keine

Lösungsmittel

ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    WaschenThe resulting solution is washed with a mixture of 100 ml each of 5% sodium sulfite solution and 5% sodium bicarbonate solution
  2. 2
    Sonstigedried
  3. 3
    Sonstigeevaporated in vacuo

Vorschrift

A solution of 4.0 g of 21-chloro-9-fluoro-11β,17-dihydroxy-16α-[(2-phenyl-2-propenyl)oxy]pregna-1,4-diene-3,20-dione in 100 ml of dichloromethane is stirred with 1.6 g of m-chloroperbenzoic acid for 1 hour at room temperature. The resulting solution is washed with a mixture of 100 ml each of 5% sodium sulfite solution and 5% sodium bicarbonate solution, dried, and evaporated in vacuo to give 4.8 g of crude 21-chloro-9-fluoro-11β,17-dihydroxy-16α-[(2-phenyloxiranyl)methoxy]pregna-1,4-diene-3,20-dione.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US03971772uspto-grants-1976_07