Reaktion #54847

Reaktionsgleichung

dimethyl sulfide

ozone

Benzhydryl 7-(1-hydroxyethyl)-3-methylene-cepham-4-carboxylate

CH2Cl2

→

benzhydryl 7-(1-hydroxyethyl)-3-hydroxy-3-cephem-4carboxylate

Lösungsmittel

oxygen

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter 1 minute at -78° the reaction mixture is treated with 5 ml
2. 2
   workup.WAITfollowed by 1 hour at 25° C
3. 3
   SonstigeThe solvent is removed under reduced pressure

Vorschrift

Benzhydryl 7-(1-hydroxyethyl)-3-methylene-cepham-4-carboxylate (4.6 g.) is dissolved in 500 ml. of CH2Cl2, cooled to -78° and treated with a stream of ozone in oxygen until a blue color persists in the reaction mixture. After 1 minute at -78° the reaction mixture is treated with 5 ml. of dimethyl sulfide and the reaction mixture is allowed to stand at -78° for 20 min. followed by 1 hour at 25° C. The solvent is removed under reduced pressure to give the crude benzhydryl 7-(1-hydroxyethyl)-3-hydroxy-3-cephem-4carboxylate.

Quelle