3-Methyl-2,3,4,5,6,7-hexahydro-1H-inden-1-one → 1,3-dimethyl-4,5,6,7-tetrahydro-1H-indene

HRID 863389Notes

Reaction equation

HRID 863389 reaction equation
[CH3:1][Li].[CH3:3][CH:4]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6](=O)[CH2:5]1>C(OCC)C>[CH3:3][C:4]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:6]([CH3:1])[CH:5]=1

Participants

4

Reactant 2

HCID 111055313-Methyl-2,3,4,5,6,7-hexahydro-1H-inden-1-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 129801691,3-dimethyl-4,5,6,7-tetrahydro-1H-indeneYield 45%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl lithium (1.5M, 96 ml) was added dropwise to a solution of 4,5,6,7-tetrahydro-1-methyl-indan-3-one (17.7 g, 0.118 mol) in 50 ml of diethyl ether under an argon atmosphere whereupon the reaction mixture was refluxed for 18 hours. The mixture after this time period was hydrolyzed and the reaction mixture extracted with diethyl ether. The ether extracts were dried over anhydrous MgSO4 and filtered. To the ether solution, 0.5 ml of 6M HCl was added and the solution stirred for one hour. After this time period the ether solution was washed with water, dried over anhydrous MgSO4, filtered and concentrated. Distillation at reduced pressure afforded 8.0 g (45 percent) of product.

Workup

  1. temperaturewas refluxed for 18 hours
  2. extractionthe reaction mixture extracted with diethyl ether
  3. dry with materialThe ether extracts were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. additionTo the ether solution, 0.5 ml of 6M HCl was added
  6. washAfter this time period the ether solution was washed with water
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. distillationDistillation at reduced pressure

Sources & evidence

ORD record
ord-313b6a4f8ac54c16820fa8a66479cbeb
Source dataset
uspto-grants-1998_02
Patent number
US05721185

Reaction notes

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