Perchloric Acid → HCID 18348556, compound

HRID 2268503Notes

Reaction equation

HRID 2268503 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:8](=O)[CH:7]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]1[CH2:31][C:30]3[C:25](=[C:26]([O:36][CH3:37])[C:27]([O:34][CH3:35])=[C:28]([O:32][CH3:33])[CH:29]=3)[C:24]1=O)[CH2:6]2.Cl(O)(=O)(=O)=O>C(O)(=O)C.[Pd]>[CH3:37][O:36][C:26]1[C:27]([O:34][CH3:35])=[C:28]([O:32][CH3:33])[CH:29]=[C:30]2[C:25]=1[CH2:24][CH:23]([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:7]1[CH2:8][C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([O:12][CH3:13])[C:10]=3[O:14][CH3:15])[CH2:6]1)[CH2:31]2

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 18348649HCID 18348649, compound

Product 1

HCID 18348556HCID 18348556, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5,6,7-trimethoxy-2-[6-(5,6,7-trimethoxy-1-oxo-2,3-dihydro-1H-2-indenyl)hexyl]-1-indanone in acetic acid (50 ml) were added 10% Pd—C (1 g) and perchloric acid (1 ml), and the reaction mixture was hydrogenated under hydrogen atmosphere (4 to 5 atm) at 50° C. for 6 hr. The catalyst was filtered off and the filtrate was concentrated in vacuo, and the residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate, water, dried, concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate) and then with recrystallization from ethyl acetate-hexane gave the entitled compound (4.5 g) as crystals.

Workup

  1. customat 50° C.
  2. customfor 6 hr
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed with saturated aqueous sodium bicarbonate, water
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  10. customwith recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5141646e618940c89d3a60ce2755f3d5
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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