반응 #834158

반응 방정식

dibenzyl ketone

cyclopentadiene

ammonium chloride

n-butyllithium

→

6,6-dibenzyl fulvene

용매

tetrahydrofuran

tetrahydrofuran

ether

n-hexane

반응 조건

후처리

1. 1
   기타Into a 100 ml Kjeldahl flask purged thoroughly with nitrogen
2. 2
   기타equipped with a dropping funnel and a magnetic stirrer
3. 3
   온도With cooling in an ice bath
4. 4
   온도With the flask cooled in an ice bath
5. 5
   workup.STIRRINGThe resulting slurry was stirred all night at room temperature
6. 6
   기타the organic phase was recovered with a separatory funnel
7. 7
   추출The water phase was extracted with ether 30 ml
8. 8
   세척The organic phase was washed twice with water 50 ml and once with a saturated salt solution 50 ml
9. 9
   건조dried over magnesium sulfate
10. 10
    여과The solution was filtered
11. 11
    기타to remove the magnesium sulfate
12. 12
    workup.DISTILLATIONthe solvent of the filtrate was distilled away
13. 13
    기타to obtain a solid
14. 14
    기타to obtain an objective brown oil in 1.10 g (12%)
15. 15
    기타yield

실험 절차

Into a 100 ml Kjeldahl flask purged thoroughly with nitrogen, equipped with a dropping funnel and a magnetic stirrer, were introduced cyclopentadiene 2.40 g (36.2 mmol) which had been subjected to cracking, and dehydrated tetrahydrofuran 50 ml. With cooling in an ice bath, 1.57 mol/L n-hexane solution of n-butyllithium, 24.3 ml (38.1 mmol), was dropwise added to the solution by means of the dropping funnel. The resulting slurry was stirred all night at room temperature. With the flask cooled in an ice bath, a solution of dibenzyl ketone 9.16 g (43.6 mmol) in 20 ml of dehydrated tetrahydrofuran, was dropwise added into the flask by means of the dropping funnel. The resulting slurry was stirred all night at room temperature. After addition of a saturated aqueous solution of ammonium chloride 50 ml and ether 50 ml, the organic phase was recovered with a separatory funnel. The water phase was extracted with ether 30 ml. The organic phase was washed twice with water 50 ml and once with a saturated salt solution 50 ml, and dried over magnesium sulfate. The solution was filtered to remove the magnesium sulfate, and the solvent of the filtrate was distilled away to obtain a solid. The residue was subjected to column chromatography to obtain an objective brown oil in 1.10 g (12%) yield. The 1H NMR spectrum and the FD-MS spectrum as measured with respect to the brown oil are given below:

출처