반응 #1077995

반응 방정식

water

sec-butyllithium

2-(2-furyl)-1,3-dioxane

tributylstannyl chloride

→

5-(1,3-Dioxan-2-yl)-2-tributylstannyl-furan

용매

THF

THF

반응 조건

후처리

1. 1
   온도cooled again to −78° C
2. 2
   온도to warm to room temperature
3. 3
   추출the mixture was extracted with ethyl acetate
4. 4
   건조The organic phase was dried with magnesium sulphate
5. 5
   농축concentrated
6. 6
   workup.DISTILLATIONthe residue was distilled (boiling point0.8 1 80° C.)
7. 7
   기타93 g were obtained

실험 절차

200 ml of sec-butyllithium (1.3M solution in cyclohexane, 260 mmol) were added dropwise to a solution of 34.4 g of 2-(2-furyl)-1,3-dioxane (224 mmol, obtainable from furfural and propane-1,3-diol) in 320 ml of THF at −70° C. in the course of 20 minutes. The solution was warmed at −20° C. for 30 minutes and then cooled again to −78° C. A solution of 60.8 ml of tributylstannyl chloride in 160 ml of THF was then added dropwise in the course of 30 minutes, after which the mixture was allowed to warm to room temperature. After 2.5 hours, water was added and the mixture was extracted with ethyl acetate. The organic phase was dried with magnesium sulphate and concentrated and the residue was distilled (boiling point0.8 1 80° C.). 93 g were obtained.

출처