Dimethyl 4-[2-(2-naphthoxy)ethoxy]benzylidenemalonate → Dimethyl 4-[2-(2-naphthoxy)ethoxy]benzylmalonate

HRID 458721Notes

Reaction equation

HRID 458721 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=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[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=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 18442910Dimethyl 4-[2-(2-naphthoxy)ethoxy]benzylidenemalonateHCID 178418361HCID 178418361, compound

Product 1

HCID 10341401Dimethyl 4-[2-(2-naphthoxy)ethoxy]benzylmalonateYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of dimethyl 4-[2-(2-naphthoxy)ethoxy]benzylidenemalonate (2.22 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 (2.10 g, 94%). HRMS calcd for C24H24O6: 408.4476. Found: 408.4475. MA calcd for C24H24O6: C, 70.58%; H, 5.92%. Found: C, 70.71%; H, 5.89%.

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-a14bfde4038b479f8bca639bb50cd241
Source dataset
uspto-grants-2007_03
Patent number
US07192970B2

Reaction notes

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