تفاعل #1681103

معادلة التفاعل

norbornene-5-carbonylchloride

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

N-butyllithium

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title compound

المردود 87.3%

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

المردود 87.3%

المذيبات

THF

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىequipped with an overhead stirrer
2. 2
   درجة الحرارةThe flask was cooled in ice
3. 3
   درجة الحرارةwhile maintaining a temperature below 100 C
4. 4
   workup.ADDITIONOnce the addition
5. 5
   workup.ADDITIONwas then slowly added over about 1.5 hours
6. 6
   درجة الحرارةwhile maintaining a temperature below 10° C
7. 7
   أخرىto reach room temperature
8. 8
   أخرىThe resulting suspension was transferred to a 4-L separatory funnel
9. 9
   غسيلwashed once with water (1 L)
10. 10
    أخرىThe organic layer was separated
11. 11
    غسيلthe aqueous wash
12. 12
    استخلاصextracted twice with ether (1 L)
13. 13
    غسيلThe combined organic solutions were washed once with water and once with brine
14. 14
    تجفيفdried over anhydrous magnesium sulfate
15. 15
    ترشيحThe suspension was filtered
16. 16
    أخرىthe solvent removed on a rotary evaporator
17. 17
    workup.DISTILLATIONthe resulting oil distilled twice at 1200 C

الإجراء التجريبي

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 100 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 HCI 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 1200 C. and 0.5 mm Hg to yield 387 g of the title compound as an oil.

المصدر