Dichlorodimethylsilane → Chloro(cyclopenta-1,3-dien-1-yl)dimethylsilane

HRID 969752Notes

Reaction equation

HRID 969752 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

HCID 6398DichlorodimethylsilaneHCID 66800589HCID 66800589, compound2×

Product 1

HCID 14894631Chloro(cyclopenta-1,3-dien-1-yl)dimethylsilaneYield 48%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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).

Workup

  1. customA white precipitate formed immediately
  2. customThe resulting reaction mixture
  3. customto separate precipitate from supernatant
  4. customThe volatiles of the isolated supernatant were removed in vacuo
  5. distillationFractional distillation

Sources & evidence

ORD record
ord-8538adcfcec14464a01ce2d33a79aa08
Source dataset
uspto-grants-2007_12
Patent number
US07307177B2

Reaction notes

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