2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-(1,3-Benzodioxol-5-yl)-6-propoxy-1H-inden-1-one

HRID 583190Notes

Reaction equation

HRID 583190 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][CH3:22])=[CH:16][CH:17]=4)[C:12](=[O:23])[CH2:11]3)=[CH:4][C:3]=2[O:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[C:18]4[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][CH3:22])=[CH:16][CH:17]=4)[C:12](=[O:23])[CH:11]=3)=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 183146271-(3,4-Methylenedioxyphenyl)-5-prop-1-yloxy-3-oxo-indane

Product 1

HCID 118089983-(1,3-Benzodioxol-5-yl)-6-propoxy-1H-inden-1-oneYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(3,4-methylenedioxyphenyl)-5-prop-1-yloxy-3-oxo-indane (2.7 g, 9.06 mmol), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (2.45 g, 10.87 mmol) in 1,4-dioxane (80 ml) was stirred at reflux for 2 h. The solvent was removed under reduced pressure and the resulting residue was dissolved in methylene chloride and filtered. The filtrate was concentrated and flash chromatography (silica gel, 3:7 ethyl acetate:hexane) afforded the title compound as a red solid (1.48 g, 55%).

Workup

  1. temperatureat reflux for 2 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe resulting residue was dissolved in methylene chloride
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-cb1c4277252a457c99ca70e287ffa261
Source dataset
uspto-grants-1999_07
Patent number
US05929106

Reaction notes

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