4-[(1E)-3-(Methyloxy)-3-oxo-1-propen-1-yl]-1-naphthalenecarboxylic acid → 4-[3-(Methyloxy)-3-oxopropyl]-1-naphthalenecarboxylic acid

HRID 1669736Notes

Reaction equation

HRID 1669736 reaction equation
[CH3:1][O:2][C:3](=[O:19])/[CH:4]=[CH:5]/[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 673480204-[(1E)-3-(Methyloxy)-3-oxo-1-propen-1-yl]-1-naphthalenecarboxylic acid2×

Product 1

HCID 673464244-[3-(Methyloxy)-3-oxopropyl]-1-naphthalenecarboxylic acidYield 289.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-[(1E)-3-(Methyloxy)-3-oxo-1-propen-1-yl]-1-naphthalenecarboxylic acid (for example as prepared for Intermediate 5) (4 g, 5.09 mmol) in 500 mL ethanol was hydrogenated over palladium on carbon (10 wt %, 1 g) for about 2 h. The catalyst was removed by filtration through Celite, the solvent evaporated and the resultant solid left overnight under vacuum to afford the title compound (3.8 g). ES+ve m/z 258 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-084969127041492e87cc392c5027146e
Source dataset
uspto-grants-2011_08
Patent number
US07989629B2

Reaction notes

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