Ethyl Acetate → HCID 67643628, compound

HRID 862947Notes

Reaction equation

HRID 862947 reaction equation
C(OC1C=C[C:15]2[C:11](=[C:12]([C:31]3[CH:36]=[CH:35][C:34]([O:37]C)=CC=3)[C:13]([C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)(C(OC)=O)[CH:14]=2)C=1)C1C=CC=CC=1.C[CH2:40][O:41][C:42]([CH3:44])=O>CCO.[Pd]>[OH:37][C:34]1[CH:35]=[C:36]2[C:14](=[CH:15][CH:11]=1)[CH:13]([C:22]1[CH:27]=[CH:26][C:25]3[O:28][CH2:29][O:30][C:24]=3[CH:23]=1)[CH:12]([C:29]([O:28][CH3:25])=[O:30])[CH:31]2[C:11]1[CH:15]=[CH:44][C:42]([O:41][CH3:40])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 88346746HCID 88346746, compound

Product 1

HCID 67643628HCID 67643628, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a degassed solution of methyl(RS)-5-benzyloxy-3-(4-methoxyphenyl)-2-(3,4-methylenedioxyphenyl)indene-2-carboxylate (6.60 g, 13.0 mmol) in EtOAc (25 ml) and EtOH (175 ml) was added 5% palladium on activated carbon (0.6 g). The resulting suspension was shaken on a Parr hydrogenator at 60 psi H2 for 20 h, at which time NMR analysis of the reaction mixture indicated that the reaction was incomplete. The catalyst was removed by filtration through a pad of Celite, and fresh 5% palladium on activated carbon (0.6 g) was added. The mixture was shaken on a Parr hydrogenator at 60 psi H2 for an additional 48 h. The catalyst was removed by filtration through a pad of Gelite, and the filtrate was concentrated under reduced pressure. The residue was crystallized from EtOAc/hexanes to afford the title compound (4.83 g, 89%); m.p. 187°-188° C.

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite, and fresh 5% palladium on activated carbon (0.6 g)
  2. additionwas added
  3. stirringThe mixture was shaken on a Parr hydrogenator at 60 psi H2 for an additional 48 h
  4. customThe catalyst was removed by filtration through a pad of Gelite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was crystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-8da95c51f6d14a649087b76930bb9880
Source dataset
uspto-grants-1998_02
Patent number
US05719182

Reaction notes

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