1,4-Cyclohexadiene → 1-(3,4-Methylenedioxyphenyl)-5-prop-1-yloxy-3-oxo-indane

HRID 583189Notes

Reaction equation

HRID 583189 reaction equation
C([C:8]1([C:25]2[CH:30]=[CH:29][C:28]3[O:31][CH2:32][O:33][C:27]=3[CH:26]=2)[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH3:20])=[CH:14][CH:15]=2)[C:10](=[O:21])[CH:9]1C([O-])=O)C1C=CC=CC=1.C1CC=CCC=1>C(O)(=O)C>[CH2:32]1[O:31][C:28]2[CH:29]=[CH:30][C:25]([CH:8]3[C:16]4[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH3:20])=[CH:14][CH:15]=4)[C:10](=[O:21])[CH2:9]3)=[CH:26][C:27]=2[O:33]1

Participants

4

Reactant 2

HCID 123431,4-CyclohexadieneHCID 86752370benzyl-(1RS,2SR)-(3,4-methylenedioxyphenyl)-5-prop-1-yloxy-3-oxo-indane-2-carboxylate

Product 1

HCID 183146271-(3,4-Methylenedioxyphenyl)-5-prop-1-yloxy-3-oxo-indaneYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of benzyl-(1RS,2SR)-(3,4-methylenedioxyphenyl)-5-prop-1-yloxy-3-oxo-indane-2-carboxylate (8.2 g, 18.4 mmol) in warm acetic acid (130 ml), was added under argon 10% Pd/C (4.1 g) followed by 1,4-cyclohexadiene (17.4 ml, 185 mmol). The reaction was exothermic and gas evolution was observed. The reaction was allowed to stir under argon at room temperature for 2 h. The mixture was filtered through a pad of celite and concentrated in vacuo. Flash chromatography of the residue (silica gel, 3:7 ethyl acetate:hexane) afforded the title compound as a pinkish solid (5.08 g, 93%).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd277ef3f72743b9a0603f0fe7015186
Source dataset
uspto-grants-1999_07
Patent number
US05929106

Reaction notes

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