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
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).
Workup
- customwas subjected to catalytic hydrogenation at room temperature under one atmospheric pressure
- filtrationThe catalyst was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe concentrate was purified by means of a silica gel column chromatography
- washFrom the fractions eluted with hexane-ethyl acetate (1:1)
Sources & evidence
- ORD record
- ord-1cd8adfbaf8a41beb827099e40da967a
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05972970
Linked notes
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