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

HRID 1953205Notes

Reaction equation

HRID 1953205 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 cyclopentadienylide 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 colorless 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 colorless oil
  8. custom(Tb.: 63-65° C., 0.02 bar (15 mmHg.))

Sources & evidence

ORD record
ord-346ea9ab426e40e3aebabbba7fe93a27
Source dataset
uspto-grants-2000_09
Patent number
US06114555

Reaction notes

Loading…