rac-(E)-5-[2-(3-methoxy-3-oxo-1-propenyl)-3-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexynyl]phenoxy]pentanoic acid ethyl ester → Rac-2-(5-ethoxy-5-oxopentyloxy)-6-[6-[(tetrahydro-2H-pyran-2-yl)oxy]hexyl]benzenepropanoic acid methyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[C:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[C:11]=1/[CH:29]=[CH:30]/[C:31]([O:33][CH3:34])=[O:32])[CH3:2]>CO.[Pd]>[CH3:34][O:33][C:31](=[O:32])[CH2:30][CH2:29][C:11]1[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[CH:13][CH:14]=[CH:15][C:10]=1[O:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:35]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A 0.86 g (1.76 mmol) sample of rac-(E)-5-[2-(3-methoxy-3-oxo-1-propenyl)-3-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexynyl]phenoxy]pentanoic acid ethyl ester was hydrogenated in 50 mL of methanol, over 50 mg of 10% palladium on carbon, at room temperature and 1 atmosphere. Rac-2-(5-ethoxy-5-oxopentyloxy)-6-[6-[(tetrahydro-2H-pyran-2-yl)oxy]hexyl]benzenepropanoic acid methyl ester, an oil, was isolated by filtration of the catalyst and concentration of the filtrate, in quantitative yield.
Sources & evidence
- ORD record
- ord-6eff29c672fe467898f5c0328f32e410
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05273999
Reaction notes
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