反応 #2507820

反応方程式

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

溶媒

hexane

hexane

THF

THF

反応条件

後処理

1. 1
   温度re-cooled to 0° C
2. 2
   その他the cooling is removed
3. 3
   温度the batch is heated
4. 4
   温度under reflux for 4 h
5. 5
   workup.ADDITIONThe batch is subsequently diluted with MTB ether
6. 6
   洗浄washed with water
7. 7
   乾燥phase is dried over sodium sulfate
8. 8
   その他evaporated
9. 9
   その他the crude product is purified by chromatography on silica gel with heptane/ethyl acetate (3:2)
10. 10
    その他The product fractions (Rf=0.5) are evaporated
11. 11
    その他the product is used without further purification

実験手順

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.

出典