반응 #2507820

반응 방정식

n-butyllithium

n-butyllithium

p-toluenesulfonyl chloride

2-(6-fluoro-3-propylchroman-7-yl)propane-1,3-diol

→

6-Fluoro-7-oxetan-3-yl-3-propylchroman

용매

hexane

hexane

THF

THF

반응 조건

후처리

1. 1
   온도re-cooled to 0° C
2. 2
   기타the cooling is removed
3. 3
   온도the batch is heated
4. 4
   온도under reflux for 4 h
5. 5
   workup.ADDITIONThe batch is subsequently diluted with MTB ether
6. 6
   세척washed with water
7. 7
   건조phase is dried over sodium sulfate
8. 8
   기타evaporated
9. 9
   기타the crude product is purified by chromatography on silica gel with heptane/ethyl acetate (3:2)
10. 10
    기타The product fractions (Rf=0.5) are evaporated
11. 11
    기타the product is used without further purification

실험 절차

3.80 g (13.7 mmol) of 2-(6-fluoro-3-propylchroman-7-yl)propane-1,3-diol are dissolved in 70 ml of THF, and 8.7 ml (13.7 mmol) of a 15 percent solution of n-butyllithium in hexane are added at 0° C. After 30 min, 2.7 g (14.2 mmol) of p-toluenesulfonyl chloride in 30 ml of THF are added, and the mixture is stirred at RT for 1 h and re-cooled to 0° C. After addition of a further 8.7 ml (13.7 mmol) of a 15% solution of n-butyllithium in hexane, the cooling is removed, and the batch is heated under reflux for 4 h. The batch is subsequently diluted with MTB ether and washed with water. The org. phase is dried over sodium sulfate and evaporated, and the crude product is purified by chromatography on silica gel with heptane/ethyl acetate (3:2). The product fractions (Rf=0.5) are evaporated, and the product is used without further purification.

출처