반응 #6030

반응 방정식

n-butyllithium

5-(4-cyanobenzoyl)-thiazole

ethyl acetate

→

1-(4-Cyanophenyl)-1-(5-thiazolyl)-ethylene

용매

ether

hexane

ether

ether

반응 조건

후처리

1. 1
   workup.ADDITIONis added at 7°
2. 2
   기타reacted with a suspension
3. 3
   workup.STIRRINGAfter stirring for 3 hours at RT
4. 4
   workup.STIRRINGthe mixture is stirred for a further 2 hours
5. 5
   온도under reflux
6. 6
   여과The solid material is filtered off with suction
7. 7
   농축the mother liquor is concentrated
8. 8
   세척the organic phase is washed in succession with 7 ml of 2N hydrochloric acid and with water
9. 9
   건조dried over sodium sulfate
10. 10
    농축concentrated
11. 11
    기타The crude product is purified by column chromatography (SiO2 0.04-0.06 mesh, 0.1 bar, hexane/ethyl acetate 2:1 to 1:1)
12. 12
    기타crystallised from hexane

실험 절차

714 mg of methyltriphenylphosphonium bromide are introduced into 6.7 ml of ether, and 0.973 ml of 1.6M n-butyllithium in hexane is added at 7°. The orange suspension is stirred at the same temperature for 1.5 hours and then reacted with a suspension, cooled to 7°, of 5-(4-cyanobenzoyl)-thiazole (Example 8a) in 3 ml of ether. After stirring for 3 hours at RT, the ether is replaced by ethyl acetate and the mixture is stirred for a further 2 hours under reflux. The solid material is filtered off with suction and the mother liquor is concentrated. The residue is taken up in methylene chloride and the organic phase is washed in succession with 7 ml of 2N hydrochloric acid and with water, dried over sodium sulfate and concentrated. The crude product is purified by column chromatography (SiO2 0.04-0.06 mesh, 0.1 bar, hexane/ethyl acetate 2:1 to 1:1) and crystallised from hexane; m.p. 71°-73°; 1H-NMR (CDCl3): δ(ppm)=5.5 (s,1H), 5.73 (s,1H) 7.54 and 7.71 (m,4H), 7.69 (s,1H), 8.78 (s,1H).

출처