반응 #446110

반응 방정식

2,2-dimethyl-4-(1,2,-4-triazol-1-yl)-butane-3-one

hept-1-yne

n-butyl lithium

→

title compound

수율 26.6%

2,2-dimethyl-3-hydroxy-3-(hept-1-yne- 1-yl)-4-(1,2,4-triazol-1-yl)-butane

수율 26.6%

용매

tetrahydrofuran

tetrahydrofuran

hexane

반응 조건

후처리

1. 1
   기타The reaction mixture was partitioned between ethyl acetate and aqueous HCl (1.0M)
2. 2
   추출The aqueous was further extracted with ethyl acetate
3. 3
   세척The combined ethyl acetate extracts were washed with water, saturated sodium bicarbonate solution and brine
4. 4
   건조dried (anhydrous MgSO4)
5. 5
   농축concentrated in-vacuo
6. 6
   기타to give a yellow oil
7. 7
   세척Chromatography on silica using gradient elution (diethyl ether 20-80% in petrol)

실험 절차

To a solution of hept-1-yne (3.9 g, 0.041 mol) in dry tetrahydrofuran (30 mls) at -70° C. under nitrogen was added n-butyl lithium (30 mls of a 1.55M solution in hexane) and the resulting mixture stirred for 1 hour. To this mixture was added a solution of 2,2-dimethyl-4-(1,2,-4-triazol-1-yl)-butane-3-one (6.8 g, 0.041 mol) in dry tetrahydrofuran (50 mls), and the resulting mixture was allowed to warm to room temperature. The reaction mixture was partitioned between ethyl acetate and aqueous HCl (1.0M). The aqueous was further extracted with ethyl acetate. The combined ethyl acetate extracts were washed with water, saturated sodium bicarbonate solution and brine, dried (anhydrous MgSO4) and then concentrated in-vacuo to give a yellow oil. Chromatography on silica using gradient elution (diethyl ether 20-80% in petrol) gave the title compound (2.87 g) as a yellow crystalline solid melting point 76°-78° C.).

출처