تفاعل #2507820

معادلة التفاعل

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

المذيبات

hexane

hexane

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةre-cooled to 0° C
2. 2
   أخرىthe cooling is removed
3. 3
   درجة الحرارةthe batch is heated
4. 4
   درجة الحرارةunder reflux for 4 h
5. 5
   workup.ADDITIONThe batch is subsequently diluted with MTB ether
6. 6
   غسيلwashed with water
7. 7
   تجفيفphase is dried over sodium sulfate
8. 8
   أخرىevaporated
9. 9
   أخرىthe crude product is purified by chromatography on silica gel with heptane/ethyl acetate (3:2)
10. 10
    أخرىThe product fractions (Rf=0.5) are evaporated
11. 11
    أخرىthe product is used without further purification

الإجراء التجريبي

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.

المصدر