HCID 53691579, compound → HCID 54247279, compound

HRID 327999Notes

Reaction equation

HRID 327999 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][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]>CO.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][CH2:4][C:3]([O:2][CH3:1])=[O:34]

Participants

4

Reactant 1

HCID 53691579HCID 53691579, compound

Product 1

HCID 54247279HCID 54247279, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A 0.9 g (1.9 mmol) sample of rac-5-[2-(3-methoxy-3-oxo-1-propenyl)-3-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexyn-1-yl]phenoxy]pentanoic acid methyl ester was hydrogenated in 60 mL of 1:1 methanol-ethyl acetate, over 70 mg of 10% palladium on carbon, at room temperature and 1 atmosphere. rac-2-(5-Methoxy-5-oxopentyloxy)-6-[6-[(tetrahydro-2-H-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-53a978d09d2144fd823dba30d0488567
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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