Chlorotrimethylsilane → HCID 53840461, compound

HRID 2186422Notes

Reaction equation

HRID 2186422 reaction equation
[CH2:1]=[CH:2][CH2:3][CH:4]=[CH2:5].C([Li])CCC.[CH3:11][Si:12]([CH3:15])([CH3:14])Cl>C(OCC)C>[CH3:11][Si:12]([CH:1]=[CH:2][CH2:3][CH:4]=[CH2:5])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 115871,4-PentadieneHCID 178418339Butyllithium

Product 1

HCID 53840461HCID 53840461, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution containing 1,4-pentadiene (5 g, 73 mol) in diethylether (100 ml) was lowered to −78° C. and n-butyllithium was added dropwise (72 mmol, 1.6M soln. in hexanes, 45 ml). The flask was stirred overnight and the temperature was allowed to warm to ambient. Solvents were removed in vacuo and a bright yellow powder was isolated. The sample was then re-dissolved in fresh diethyl ether (100 ml) and the temperature was lowered to −78° C. Trimethylchlorsilane (7.9 mmol, 10 ml) was added dropwise. The reaction was allowed to slowly warm to ambient and the flask contents stirred overnight. Solvents were removed in vacuo. 1M-NMR: CTHF-d8) d, ppm; 6.25 (m, 2H), 5.9 (m, 2H), 5.65 (m, 2H), 4.95 (s, 1H), 4.90 (s, 1H), 4.80 (s, 1H), 4.75 (s, 1H), 1.5 (d, 2H), 0 (m, 9H).

Workup

  1. customwas lowered to −78° C.
  2. temperatureto warm to ambient
  3. customSolvents were removed in vacuo
  4. customa bright yellow powder was isolated
  5. customwas lowered to −78° C
  6. temperatureto slowly warm to ambient and the flask contents
  7. stirringstirred overnight
  8. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-9f29d3491236449f8cf874829758e0d5
Source dataset
uspto-grants-2002_06
Patent number
US06403772B1

Reaction notes

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