تفاعل #75598

معادلة التفاعل

ammonium chloride

vinylmagnesium bromide

THF

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

THF

→

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

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةunder heating
2. 2
   درجة الحرارةreflux
3. 3
   درجة الحرارةunder ice-cooling
4. 4
   استخلاصextracted with ethyl acetate
5. 5
   غسيلwashed twice with brine
6. 6
   أخرىThe solvent was removed
7. 7
   أخرىthe resulting residue was purified by silica gel column chromatography

الإجراء التجريبي

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.

المصدر