(Z)-2-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]-2-propenyl]-1,3-dioxane → 2-[3-[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propyl]-1,3-dioxane
Reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]\[CH2:24][CH:25]2[O:30][CH2:29][CH2:28][CH2:27][O:26]2)=[CH:18][CH:17]=1>[C].[Pd].C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][CH2:24][CH:25]2[O:30][CH2:29][CH2:28][CH2:27][O:26]2)=[CH:20][CH:21]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of (Z)-2-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]-2-propenyl]-1,3-dioxane (5.0 g), palladium-carbon (5%, 0.1 g) and ethanol (100 ml) was subjected to catalytic hydrogenation at room temperature under one atmospheric pressure. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was purified by means of a silica gel column chromatography. From the fractions eluted with hexane-ethyl acetate (1:1), 2-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propyl]-1,3-dioxane (4.8 g, 96%) was obtained. NMR (δ ppm in CDCl3): 1.25-1.4(1H,m), 1.5-1.8(4H,m), 1.9-2.2(1H,m), 2.37(3H,s), 2.54(2H,t,J=7 Hz), 2.96(2H,t,J=6.5 Hz), 3.65-3.85(2H,m), 4.0-4.15(2H,m), 4.21(2H,t,J=6.5 Hz), 4.50(1H,t,J=5 Hz), 6.80(2H,d,J=9 Hz), 7.06(2H,d,J=9 Hz), 7.35-7.5(3H,m), 7.9-8.0(2H,m).