Reaction #1435716

Reaction equation

sodium cyclopentadienide

2-trimethylsiloxy-1-bromo-ethane

ammonium chloride

→

(2-trimethylsiloxy-ethyl)-cyclopentadiene

Yield 64.0%

Solvents

tetrahydrofurane

tetrahydrofurane

Conditions

Workup

1. 1
   TemperatureThe reaction is maintained
2. 2
   ExtractionThe organic phase is extracted
3. 3
   Dryingdried with magnesium sulphate
4. 4
   workup.DISTILLATIONthe volatile part is distilled under vacuum
5. 5
   Otherobtaining an orange oil
6. 6
   workup.DISTILLATIONThis oil is distilled in order
7. 7
   Otherto obtain a colourless oil
8. 8
   Other(Tb.: 63–65° C., 0.02 bar (15 mmHg.))

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).

Source