Ethyl 3-methylpenta-2,4-dienoate → 3-{3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-but-2-enoic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH:5]=[C:6]([CH3:9])[CH:7]=[CH2:8])[CH3:2].[CH3:11][C:12]1[CH:21]=[C:20]([CH2:22][O:23][C:24]2[CH:32]=[CH:31][C:27]([CH:28]=[N:29][OH:30])=[CH:26][CH:25]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1>>[CH2:1]([O:3][C:4](=[O:10])[CH:5]=[C:6]([CH:7]1[O:30][N:29]=[C:28]([C:27]2[CH:26]=[CH:25][C:24]([O:23][CH2:22][C:20]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=[C:12]([CH3:11])[CH:21]=3)=[CH:32][CH:31]=2)[CH2:8]1)[CH3:9])[CH3:2]Participants
3
Procedure
Following a procedure analogous to that used in Example step 1c, but using 3-methyl-penta-2,4-dienoic acid ethyl ester and 4-(2-methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime from step 1b, the crude reaction was partitioned between ethyl acetate and water, and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel eluting ethyl acetate:hexane (gradient) to give 3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-but-2-enoic acid ethyl ester (0.93 g, 84%) as a mixture of diasteromers. MS found: (M+H)+=431.
Workup
- customthe crude reaction
- customwas partitioned between ethyl acetate and water
- washthe organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customto give an oil
- customThe product was purified by FCC on silica gel
- washeluting ethyl acetate
Sources & evidence
- ORD record
- ord-f49455f4ed8740f19ab5953aad2d8dea
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07125870B2
Reaction notes
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