반응 #75598

반응 방정식

ammonium chloride

vinylmagnesium bromide

THF

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

THF

→

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

반응 조건

후처리

1. 1
   온도under heating
2. 2
   온도reflux
3. 3
   온도under ice-cooling
4. 4
   추출extracted with ethyl acetate
5. 5
   세척washed twice with brine
6. 6
   기타The solvent was removed
7. 7
   기타the resulting residue was purified by silica gel column chromatography

실험 절차

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.

출처