1,3-Cyclohexadiene → 2,3-Dihydro-4,7-dimethoxy-1H-indene

HRID 1252987Notes

Reaction equation

HRID 1252987 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=O.C1CCC=CC=1>C1(C)C=CC=CC=1>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]2[C:8]=1[CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 116051,3-CyclohexadieneHCID 6060124,7-dimethoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 126541332,3-Dihydro-4,7-dimethoxy-1H-indene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of intermediate A (1 g, 6 mmole), 1,3-cyclohexadiene (0.6 ml, 6 mmole), and toluene (15 ml) was refluxed about 15 hours under a nitrogen atmosphere. The solvent was removed under reduced pressure to yield 1.5 g of crude Diels-Alder adduct (intermediate B), which was used directly in the next step.

Workup

  1. temperaturewas refluxed about 15 hours under a nitrogen atmosphere
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-22717950577c41cf82522d615a371747
Source dataset
uspto-grants-1988_05
Patent number
US04746607

Reaction notes

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