Reaction #1153

Reaction equation

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

→

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

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Otherfollowed 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
   TemperatureAfter 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
   Extractionfollowed by extraction with ethyl acetate
8. 8
   WashAfter the ethyl acetate layer was washed with water
9. 9
   Dryingdried (MgSO4)
10. 10
    workup.DISTILLATIONthe solvent was distilled off
11. 11
    WashFrom the fraction eluted with ethyl acetate-chloroform (1:5

Procedure

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%).

Source