Dichlorodimethylsilane → Chloro(cyclopenta-1,3-dien-1-yl)dimethylsilane
Reaction equation
[Si:1]([CH3:5])([CH3:4])(Cl)[Cl:2].[CH:6]1[CH2:10][CH:9]=[CH:8][CH:7]=1.[Na]>C(OCC)C>[Cl:2][Si:1]([C:7]1[CH2:6][CH:10]=[CH:9][CH:8]=1)([CH3:5])[CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of Me2SiCl2 (225 mL, 1.86 mol) in 450 mL of diethyl ether was cooled to 0° C., after which a sodium cyclopentadiene (compound 1) solution (1.68 M, 950 mL, 1.60 mol) was added dropwise. A white precipitate formed immediately. The reaction was allowed to warm up to room temperature and was stirred for an additional 4 hours. The resulting reaction mixture was centrifuged to separate precipitate from supernatant. The volatiles of the isolated supernatant were removed in vacuo. Fractional distillation yielded 122.76 g (48%) of the desired product as a colorless liquid (48-52° C./15 mmHg).