반응 #610503

반응 방정식

(2E)-3-{4-[(6-hydroxyhexyl)oxy]-3-methoxyphenyl}prop-2-enoate

pyridine

MeOH

3,5-dinitrobenzoyl chloride

→

6-{2-methoxy-4-[(1E)-3-methoxy-3-oxoprop-1-enyl]phenoxy}hexyl 3,5-dinitrobenzoate

수율 64.0%

용매

toluene

반응 조건

후처리

1. 1
   온도The solution is then heated up to 60° C.
2. 2
   workup.STIRRINGThe suspension is stirred at room temperature for 1 hour and at 0° C. for 1 hour
3. 3
   여과The precipitate is filtered off

실험 절차

17.9 g (78 mmol) of 3,5-dinitrobenzoyl chloride are dissolved in 147 mL of toluene and 20 drops of DMF were incorporated. 24 g (78 mmol) of (2E)-3-{4-[(6-hydroxyhexyl)oxy]-3-methoxyphenyl}prop-2-enoate, 0.475 g (4 mmol) of 4-dimethylaminopyridine and 9.23 g (117 mmol) of pyridine are added. The mixture is stirred at room temperature for 96 hours. The solution is then heated up to 60° C. and 58 ml of MeOH are added. The suspension is stirred at room temperature for 1 hour and at 0° C. for 1 hour. The precipitate is filtered off. Chromatography of the residue using toluene: ethyl acetate 19:1 following by toluene: ethyl acetate 9:1 yielded 25 g (64%) of pure 6-{2-methoxy-4-[(1E)-3-methoxy-3-oxoprop-1-enyl]phenoxy}hexyl 3,5-dinitrobenzoate as an orange powder.

출처