Titanocene dichioride → Dimethyl titanocene

HRID 399748Notes

Reaction equation

HRID 399748 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-d61f4d80d4f142d7925bc79b841615bf
Source dataset
uspto-grants-1998_10
Patent number
US05824678

Reaction notes

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