Reaktion #463184

Reaktionsgleichung

hydrochloric acid

N-[1(S)-benzyl-3-hydroxy-2(R)-(methylsulphonyloxy)propyl]phthalimide

sodium hydride

sodium hydride

→

2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane

Ausbeute 41.2%

Lösungsmittel

tetrahydrofuran

dichloromethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe stirring was continued for 3.5 hours
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with saturated sodium chloride solution
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe residue was chromatographed on silica gel
6. 6
   Waschenfor the elution

Vorschrift

2.16 g of N-[1(S)-benzyl-3-hydroxy-2(R)-(methylsulphonyloxy)propyl]phthalimide were added to a stirred suspension of 200 mg of sodium hydride (80% dispersion in mineral oil) in 50 ml of dry tetrahydrofuran and the mixture was stirred at 20° C. for 2 hours. A further 100 mg of sodium hydride were added and the stirring was continued for 3.5 hours. The mixture was diluted with dichloromethane and water and the pH of the aqueous layer was adjusted to 7 by adding 2M hydrochloric acid. The organic layer was separated, washed with saturated sodium chloride solution and evaporated. The residue was chromatographed on silica gel using ethyl acetate/n-hexane (1:2) for the elution to give 0.67 g of 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane as a white solid, MS: m/e 294 [M+H]+.

Quelle