반응 #1153

반응 방정식

(E)-ethyl 3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]acrylate

→

3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]propanol

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타followed by catalytic reduction at room temperature and under an atmospheric pressure of 1 atm
2. 2
   여과After the catalyst was filtered off
3. 3
   workup.ADDITIONsodium borohydride (0.61 g) was added to the filtrate
4. 4
   workup.ADDITIONfollowed by dropwise addition of methanol (10 ml) under refluxing conditions
5. 5
   온도After heating under refluxing conditions for 1 hour
6. 6
   workup.ADDITIONthe reaction mixture was poured over water and neutralized with 2N hydrochloric acid
7. 7
   추출followed by extraction with ethyl acetate
8. 8
   세척After the ethyl acetate layer was washed with water
9. 9
   건조dried (MgSO4)
10. 10
    workup.DISTILLATIONthe solvent was distilled off
11. 11
    세척From the fraction eluted with ethyl acetate-chloroform (1:5

실험 절차

To a solution of (E)-ethyl 3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]acrylate (1.30 g) in tetrahydrofuran (50 ml), palladium-carbon (5%, 0.70 g) was added, followed by catalytic reduction at room temperature and under an atmospheric pressure of 1 atm. After the catalyst was filtered off, sodium borohydride (0.61 g) was added to the filtrate, followed by dropwise addition of methanol (10 ml) under refluxing conditions. After heating under refluxing conditions for 1 hour, the reaction mixture was poured over water and neutralized with 2N hydrochloric acid, followed by extraction with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off; the residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-chloroform (1:5, v/v), 3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]propanol was obtained as an oily substance (0.90 g, 77%).

출처