Reaction #710049

Reaction equation

Chlorotrimethylsilane

Sodium cyclopentadienide

→

bis(trimethylsilyl)cyclopentadiene

trimethylsilylcyclopentadiene

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONThe reaction mixture is poured into 150 ml of cold,
2. 2
   workup.DISTILLATIONdistilled water and trimethylsilylcyclopentadiene
3. 3
   Extractionis extracted into diethyl ether
4. 4
   OtherThe extract is rotary evaporated
5. 5
   Otherto remove the ethereal solvent
6. 6
   workup.DISTILLATIONdistilled

Procedure

Trimethylsilylcyclopentadiene and bis(trimethylsilyl)cyclopentadiene are prepared by the procedures of Kraihanzel et al., J. Amer. Chem. Soc., 90, 4701 (1968) and I. M. Pribytkova et al., J. of Organometallic Chem., 30, C57-C60 (1971). Sodium cyclopentadienide (44 g, 0.50 mole) is added to 150 ml of tetrahydrofuran. Chlorotrimethylsilane (54 g, 0.5 mole) is added dropwise slowly to the reaction and the stirring is continued for 3 hours. The reaction mixture is poured into 150 ml of cold, distilled water and trimethylsilylcyclopentadiene is extracted into diethyl ether. The extract is rotary evaporated to remove the ethereal solvent and the residue is vacuum distilled to give trimethylsilylcyclopentadiene, b.p. 41° C.-43° C. (16 mm).

Source