HCID 11596697, compound → HCID 9844554, compound

HRID 458715Notes

Reaction equation

HRID 458715 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][O:14][C:15]1[CH:30]=[CH:29][C:18]([CH:19]=[C:20]([C:25]([O:27][CH3:28])=[O:26])[C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=1.[H][H]>CO.O1CCOCC1.[Pd]>[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][O:14][C:15]1[CH:30]=[CH:29][C:18]([CH2:19][CH:20]([C:25]([O:27][CH3:28])=[O:26])[C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 11596697HCID 11596697, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9844554HCID 9844554, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of dimethyl 4-[2-(5,6,7,8-tetrahydro-2-naphthoxy)ethoxy]benzylidenemalonate (2.24 g, 5.47 mmol) in a mixture of methanol (20 ml) and 1,4-dioxane (150 ml) is added 5% palladium on charcoal (1.20 g). Then the mixture is stirred under an atmosphere of hydrogen at room temperature until hydrogen uptake ceased. The solution is filtered through Celite, and the filtrate is evaporated under a vacuum. The residue is crystallized from ethyl acetate to give the title compound (2.16 g, 96%). HRMS calcd for C24H28O6: 412.4827. Found: 412.4825. MA calcd for C24H28O6: C, 69.99%; H, 6.84%. Found: C, 69.82%; H, 6.88%.

Workup

  1. filtrationThe solution is filtered through Celite
  2. customthe filtrate is evaporated under a vacuum
  3. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-56155d3bfb2e4086ac84946f6bc6d326
Source dataset
uspto-grants-2007_03
Patent number
US07192970B2

Reaction notes

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