Reaktion #75598

Reaktionsgleichung

ammonium chloride

vinylmagnesium bromide

THF

(5S)-5-[(trityloxy)methyl]tetrahydro-2-furanone

THF

→

(2S)-1-(trityloxy)-5-vinyl-6-heptene-2,5-diol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder heating
2. 2
   Temperaturreflux
3. 3
   Temperaturunder ice-cooling
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   Waschenwashed twice with brine
6. 6
   SonstigeThe solvent was removed
7. 7
   Sonstigethe resulting residue was purified by silica gel column chromatography

Vorschrift

26.9 g of (5S)-5-[(trityloxy)methyl]tetrahydro-2-furanone was dissolved in 200 ml THF, 300 ml solution of 1 M vinylmagnesium bromide in THF was added thereto at room temperature, and it was stirred for 1.5 hr under heating and reflux. After the reaction was completed, saturated aqueous ammonium chloride was added thereto under ice-cooling, extracted with ethyl acetate, and then washed twice with brine. The solvent was removed and the resulting residue was purified by silica gel column chromatography to give 13.0 g of (2S)-1-(trityloxy)-5-vinyl-6-heptene-2,5-diol.

Quelle