Titanocene dichioride → Dimethyl titanocene

HRID 976336Notes

Reaction equation

HRID 976336 reaction equation
[Cl-].[Cl-].[CH-:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[Ti+2:13].C[Li]>CCOCC.O>[CH3:8][C-:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[C-:8]1([CH3:3])[CH:12]=[CH:11][CH:10]=[CH:9]1.[Ti+2:13]

Participants

5

Reactant 2

HCID 124040768Titanocene dichiorideHCID 178418348HCID 178418348, compound

Product 1

HCID 129651941Dimethyl titanoceneYield 197%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 2.49 g (10.0 mmol) of titanocene dichloride in 50 ml of ether in the dark at 0° C. was treated with 17.5 ml of 1.4M methyllithium solution in ether maintaining the internal temperature below 5° C. The resulting yellow/orange mixture was stirred at room temperature for 30 minutes and the reaction was quenched by slowly adding 25 g of ice. The quenched reaction mixture was diluted with 50 ml of ether and 25 ml of water and the layers were separated. The organic layer was dried over magnesium sulfate and concentrated in vacuo to afford 2.03 g (98%) of the title compound as a light-sensitive solid. The dimethyl titanocene could be stored as a solution in toluene at 0° C. for at least 2 weeks without apparent chemical degradation. 1H NMR (200 MHz, CDCl3) δ -0.15 (6H, s), 6.06 (10H, s).

Workup

  1. customthe reaction was quenched
  2. additionby slowly adding 25 g of ice
  3. customThe quenched reaction mixture
  4. customthe layers were separated
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-316d802ded7646e096a67b3c96cb55ae
Source dataset
uspto-grants-1997_03
Patent number
US05612337

Reaction notes

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