rac-4-[2-(3-methoxy-3-oxo-1-propenyl)-3-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexynyl]phenoxy]butanoic acid ethyl ester → rac-2-(4-Ethoxy-4-oxobutoxy)-6-[6-[(tetrahydro-2H-pyran-2-yl)oxy]hexyl]benzenepropanoic acid methyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[C:10]=1[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[O:31])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH3:33][O:32][C:30](=[O:31])[CH2:29][CH2:28][C:10]1[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:34]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A 9.73 g (ca. 20 mmol) sample of crude rac-4-[2-(3-methoxy-3-oxo-1-propenyl)-3-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexynyl]phenoxy]butanoic acid ethyl ester from the preceding example was hydrogenated in 275 mL of ethyl acetate, over 0.75 g of 10% palladium on carbon, at room temperature and 1 atmosphere, for 24 hr. rac-2-(4-Ethoxy-4-oxobutoxy)-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 (9.74 g).
Sources & evidence
- ORD record
- ord-f6961f0843fc4a21ae41ffa7b49e2405
- Source dataset
- uspto-grants-1995_10
- Patent number
- US05457124
Reaction notes
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