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

HRID 54887Notes

Reaction equation

HRID 54887 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 45.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl lithium (96 mL, 1.5M, 0.144 mol) 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 was hydrolyzed, and 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 was 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. extractionextracted 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-45d121d831734b0783ea716e112a8f1a
Source dataset
uspto-grants-1997_04
Patent number
US05624878

Reaction notes

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