HCID 59590766, compound → HCID 59590767, compound

HRID 2098959Notes

Reaction equation

HRID 2098959 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14]/[C:15]/2=[CH:18]\[C:19]([O:21][CH3:22])=[O:20])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][CH:15]2[CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 59590766HCID 59590766, compound

Product 1

HCID 59590767HCID 59590767, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under hydrogen, a mixture of (E)-methyl 2-(6-(benzyloxy)-2,3-dihydroinden-1-ylidene)acetate (1.3) (1.64 g, 5.57 mmol), palladium on carbon (10%) (0.462 g, 3.90 mmol) in MeOH (30 mL) were stirred for 24 hours. The mixture was then filtered through silica gel to remove the Pd—C, eluting with EtOAc. After removing solvent by rotary evaporation, the residue was purified using column chromatography (1:1 EtOAc/hexane). Product 1.4 was obtained in 68% yield as a colorless oil.

Workup

  1. filtrationThe mixture was then filtered through silica gel
  2. customto remove the Pd—C
  3. washeluting with EtOAc
  4. customAfter removing solvent
  5. customby rotary evaporation
  6. customthe residue was purified

Sources & evidence

ORD record
ord-ad60695382604aa0af26673dfed734bd
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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