HCID 18442911, compound → HCID 18442912, compound

HRID 458709Notes

Reaction equation

HRID 458709 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([O:14][CH2:15][CH2:16][O:17][C:18]3[CH:33]=[CH:32][C:21]([CH:22]=[C:23]([C:28]([O:30][CH3:31])=[O:29])[C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=3)[CH:5]=[CH:4][C:3]1=2.[H][H]>CO.O1CCOCC1.[Pd]>[CH3:1][C:2]1([CH3:34])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([O:14][CH2:15][CH2:16][O:17][C:18]3[CH:19]=[CH:20][C:21]([CH2:22][CH:23]([C:24]([O:26][CH3:27])=[O:25])[C:28]([O:30][CH3:31])=[O:29])=[CH:32][CH:33]=3)[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 2

HCID 18442911HCID 18442911, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18442912HCID 18442912, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of dimethyl 4-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoxy)ethoxy]benzylidenemalonate (2.55 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 (2.45 g, 96%). HRMS calcd for C28H36O6: 468.5902. Found: 468.5905. MA calcd for C28H36O6: C, 71.77%; H, 7.74%. Found: C, 71.52%; H, 7.76%.

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-74844e7647de4960ad0e23fd5a588037
Source dataset
uspto-grants-2007_03
Patent number
US07192970B2

Reaction notes

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