反应 #833533

反应方程式

norbornene-5-carbonylchloride

1,1,1-trifluoro-2-trifluoromethyl-2,4-pentanediol

N-butyllithium

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title compound

收率 87.3%

1,1,1-trifluoro-2-hydroxy-2-trifluoromethyl-4-pentyl norbornene-5-carboxylate

收率 87.3%

溶剂

THF

THF

THF

反应条件

后处理

1. 1
   其他equipped with an overhead stirrer
2. 2
   温度The flask was cooled in ice
3. 3
   温度while maintaining a temperature below 10° C
4. 4
   workup.ADDITIONOnce the addition
5. 5
   workup.ADDITIONwas then slowly added over about 1.5 hours
6. 6
   温度while maintaining a temperature below 10° C
7. 7
   其他to reach room temperature
8. 8
   其他The resulting suspension was transferred to a 4-L separatory funnel
9. 9
   洗涤washed once with water (1 L)
10. 10
    其他The organic layer was separated
11. 11
    洗涤the aqueous wash
12. 12
    萃取extracted twice with ether (1 L)
13. 13
    洗涤The combined organic solutions were washed once with water and once with brine
14. 14
    干燥dried over anhydrous magnesium sulfate
15. 15
    过滤The suspension was filtered
16. 16
    其他the solvent removed on a rotary evaporator
17. 17
    workup.DISTILLATIONthe resulting oil distilled twice at 120° C.

实验过程

N-butyllithium (1600 ml) (2.56 mol, 1.6M solution in hexanes) was added to a 3-L, three-necked round bottomed flask equipped with an overhead stirrer, a digital thermometer, a 500-mL capacity constant-pressure dropping funnel and a nitrogen inlet. The dropping funnel was charged with a solution of 1,1,1-trifluoro-2-trifluoromethyl-2,4-pentanediol (289 g, 1.28 mol) in anhydrous THF (250 ml). The flask was cooled in ice and the THF solution was slowly added over about 2 hours, while maintaining a temperature below 10° C. Once the addition was complete, the dropping funnel was recharged with a solution of norbornene-5-carbonylchloride (201 g, 1.28 mol) in anhydrous THF (250 ml), which was then slowly added over about 1.5 hours, while maintaining a temperature below 10° C. The solution was allowed to reach room temperature with stirring overnight. The resulting suspension was transferred to a 4-L separatory funnel and washed once with water (1 L). The organic layer was separated and the aqueous wash was adjusted to pH 6 (litmus) with concentrated HCl and extracted twice with ether (1 L). The combined organic solutions were washed once with water and once with brine and dried over anhydrous magnesium sulfate. The suspension was filtered, the solvent removed on a rotary evaporator and the resulting oil distilled twice at 120° C. and 0.5 mm Hg to yield 387 g of the title compound as an oil.

来源