Ammonium Chloride → (2-Trimethylsiloxy-ethyl)-cyclopentadiene

HRID 1348534Notes

Reaction equation

HRID 1348534 reaction equation
[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Na+].[CH3:7][Si:8]([CH3:14])([CH3:13])[O:9][CH2:10][CH2:11]Br.[Cl-].[NH4+]>O1CCCC1>[CH3:7][Si:8]([CH3:14])([CH3:13])[O:9][CH2:10][CH2:11][C:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 78681Sodium, 2,4-cyclopentadien-1-yl-HCID 587231(2-Bromoethoxy)trimethylsilane

Product 1

HCID 23303830(2-Trimethylsiloxy-ethyl)-cyclopentadieneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

150 ml of a 2.3 M sodium cyclopentadienide solution in tetrahydrofurane (346 mmol) is slowly added to a solution of 68.2 g (346 mmol) 2-trimethylsiloxy-1-bromo-ethane in tetrahydrofurane. The immediate formation of a pinkish solid is observed. The reaction is maintained under stirring for 12 hours. Then, an ammonium chloride aqueous solution is added. The organic phase is extracted, dried with magnesium sulphate and the volatile part is distilled under vacuum, obtaining an orange oil. This oil is distilled in order to obtain a colourless oil. (Tb.: 63–65° C., 0.02 bar (15 mmHg.)). (40.3 g, 221 mmol. Yield:64%). 1H-NMR (CDCl3): 6.50–6.00 (m,3H), 3.75 (m, 2H), 2.95 (m, 2H), 2.65 (m, 2H), 0.15 (s, 9H).

Workup

  1. temperatureThe reaction is maintained
  2. extractionThe organic phase is extracted
  3. dry with materialdried with magnesium sulphate
  4. distillationthe volatile part is distilled under vacuum
  5. customobtaining an orange oil
  6. distillationThis oil is distilled in order
  7. customto obtain a colourless oil
  8. custom(Tb.: 63–65° C., 0.02 bar (15 mmHg.))

Sources & evidence

ORD record
ord-469b483e9ff34801a3b22b0cdf916f1d
Source dataset
uspto-grants-2007_05
Patent number
US07211538B2

Reaction notes

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