Reaktion #1153

Reaktionsgleichung

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

→

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

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefollowed by catalytic reduction at room temperature and under an atmospheric pressure of 1 atm
2. 2
   FiltrationAfter 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
   TemperaturAfter 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
   Extraktionfollowed by extraction with ethyl acetate
8. 8
   WaschenAfter the ethyl acetate layer was washed with water
9. 9
   Trocknendried (MgSO4)
10. 10
    workup.DISTILLATIONthe solvent was distilled off
11. 11
    WaschenFrom the fraction eluted with ethyl acetate-chloroform (1:5

Vorschrift

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%).

Quelle