Reaction #1435720

Reaction equation

ammonium chloride

sodium cyclopentadienylide

3-bromo-1-trimethylsiloxypropane

→

(3-trimethylsiloxypropyl)-cyclopentadiene

Yield 43.0%

Solvents

tetrahydrofurane

Conditions

Workup

1. 1
   TemperatureThe reaction is maintained
2. 2
   Extractionthe organic phase is extracted
3. 3
   Concentrationconcentrated to dryness in order
4. 4
   Otherto give an orange oil

Procedure

To 50 ml of a 2.3 M solution of sodium cyclopentadienylide (115 mmol), a solution of 24.3 g (115 mmol) of 3-bromo-1-trimethylsiloxypropane in tetrahydrofurane is added. The quick formation of a pinkish solid is observed. The reaction is maintained under stirring for 12 hours and then it is neutralised with an ammonium chloride solution; the organic phase is extracted and concentrated to dryness in order to give an orange oil. (9.8 g, 50 mmol. Yield: 43%). 1H-NMR (CDCl3): 6.47–6.00 (m, 3H), 3.62 (m, 2H), 2.95 (m, 1H), 2.87 (m, 1H), 2.43 (m, 2H), 1.80 (m, 2H), 0.17 (s, 9H).

Source