Cyclopentadiene → Methoxydimethylsilylcyclopentadiene

HRID 1456913Notes

Reaction equation

HRID 1456913 reaction equation
[Na].[CH:2]1[CH2:6][CH:5]=[CH:4][CH:3]=1.CO[Si:9]([CH3:12])([CH3:11])Cl.C1C[O:16][CH2:15]C1>C1(C)C=CC=CC=1>[CH3:15][O:16][C:3]1[CH:2]=[CH:6][CH2:5][C:4]=1[SiH:9]([CH3:12])[CH3:11]

Participants

6

Conditions

Temperature
0 °C

Procedure

16.8 ml (0.22 moles) of a suspension of sodium in toluene at 30% are charged into a 250 ml flask. The mixture is diluted with 100 ml of THF and cooled to 0° C. 18.5 ml (0.22 moles) of cyclopentadiene diluted in 50 ml of THF are slowly added dropwise (about 60 minutes). The resulting solution is left under stirring at room temperature for a whole night, is then cooled to 0° C. and 29 ml (0.22 moles) of methoxydimethylchlorosilane fresh distillate (PETRARCH: 90%) are slowly added dropwise. The reaction is carried out at 0° C. for 3 hours. After filtration of the salt formed and evaporation of the solvent, a dark yellow oily liquid is obtained which, on distillation at 160°-162° C. gives 7.5 g of the desired product with a purity of 95.5% (GC), and a yield of 24%.

Workup

  1. additionare slowly added dropwise (about 60 minutes)
  2. waitThe resulting solution is left
  3. temperatureis then cooled to 0° C.
  4. filtrationAfter filtration of the salt
  5. customformed
  6. customevaporation of the solvent
  7. customa dark yellow oily liquid is obtained which
  8. distillationon distillation at 160°-162° C.

Sources & evidence

ORD record
ord-975e56723ee748a6a679d1798a13d398
Source dataset
uspto-grants-1998_12
Patent number
US05846895

Reaction notes

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