Ethyl Acetate → HCID 18933568, compound

HRID 1598143Notes

Reaction equation

HRID 1598143 reaction equation
C([O:8][C:9]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:10]=1[C:11]([C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][CH3:22])[CH:16]=[CH:15][C:14]=1[C:23](=[O:33])[C:24]1[CH:29]=[CH:28][C:27]2[O:30][CH2:31][O:32][C:26]=2[CH:25]=1)=[O:12])C1C=CC=CC=1.C(OCC)(=O)C>[Pd].CCCCCC>[OH:8][C:9]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:10]=1[C:11]([C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][CH3:22])[CH:16]=[CH:15][C:14]=1[C:23](=[O:33])[C:24]1[CH:29]=[CH:28][C:27]2[O:30][CH2:31][O:32][C:26]=2[CH:25]=1)=[O:12]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 18933567HCID 18933567, compound

Product 1

HCID 18933568HCID 18933568, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8058HexaneSolvent

Procedure

To a solution of 1-(2-benzyloxy-4-methoxybenzoyl)-2-(3,4-methylenedioxybenzoyl)-5-prop-1-yloxybenzene (0.437 g, 0.84 mmol) in a mixture 1:1 ethyl acetate:hexane (20 ml) was added 10% Pd/C (0.040 g) and the mixture was shaken under hydrogen atmosphere at 60 psi for 24 h. The reaction mixture was filtered through a pad of celite and the filtrate dried (MgSO4). After removing the solvent under reduced pressure, flash chromatography of the residue (silica gel, 3:7 ethyl acetate:hexane) afforded the title compound as a pale yellow oil (0.270 g, 72%).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. dry with materialthe filtrate dried (MgSO4)
  3. customAfter removing the solvent under reduced pressure, flash chromatography of the residue (silica gel, 3:7 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-a21c02c18610465581d0777f1a1bae50
Source dataset
uspto-grants-1998_04
Patent number
US05736564

Reaction notes

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