Water → 3-Methylindene

HRID 850123Notes

Reaction equation

HRID 850123 reaction equation
[CH-:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Li+].[CH3:11]OS(OC)(=O)=O.O>C(OCC)C>[CH3:11][C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11116044Lithium, 1H-inden-1-yl-

Product 1

HCID 130253-MethylindeneYield 94.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium indenide (9.60 g, 0.0786 moles) in diethylether (100 mL) was added dropwise to a solution of dimethylsulfate (9.91 g, 0.0786 moles) in diethylether (125 mL) over a period of 15 minutes. After the addition was complete, H2O (150 mL) was added to the reaction. The organic layer was then separated and washed with H2O (2×100 mL). Drying over MgSO4 followed by filtration and solvent removal yielded the desired product as a yellow oil (9.68 g, 94.7 percent).

Workup

  1. additionAfter the addition
  2. customThe organic layer was then separated
  3. washwashed with H2O (2×100 mL)
  4. dry with materialDrying over MgSO4
  5. filtrationfollowed by filtration and solvent removal

Sources & evidence

ORD record
ord-81f03ef69290439f81d9f3c3a336db35
Source dataset
uspto-grants-2000_01
Patent number
US06015868

Reaction notes

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