(E)-3-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]-2-propen-1-ol → 3-[5-(5-Methylphenyl-4-oxazolylmethoxy)-2-benzofuranyl]propanol
Reaction equation
C[C:2]1[O:6][C:5](C2C=CC=CC=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]2[O:22][C:21](/[CH:23]=[CH:24]/[CH2:25][OH:26])=[CH:20][C:19]=2[CH:27]=1>O1CCCC1.[C].[Pd]>[CH3:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:13]([C:3]2[N:4]=[CH:5][O:6][CH:2]=2)[O:14][C:15]2[CH:16]=[CH:17][C:18]3[O:22][C:21]([CH2:23][CH2:24][CH2:25][OH:26])=[CH:20][C:19]=3[CH:27]=2)[CH:27]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (E)-3-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]-2-propen-1-ol (2.00 g) in tetrahydrofuran (100 ml), palladium-carbon (5%, 0.30 g) was added, followed by catalytic reduction at room temperature and under an atmospheric pressure of 1 atm. After the catalyst was filtered off, the filtrate was concentrated to yield 3-[5-(5-methylphenyl-4-oxazolylmethoxy)-2-benzofuranyl]propanol (yield 93%), which was then recrystallized from acetone-isopropyl ether to yield colorless prisms having a melting point of 101° to 102° C.