Tetraethoxysilane → Trifluorovinyl triethoxysilane

HRID 392940Notes

Reaction equation

HRID 392940 reaction equation
[C:1](=[C:4](Cl)[F:5])([F:3])[F:2].[Li]C(CC)C.[Si:12](OCC)([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>CCOCC>[C:1](=[C:4]([Si:12]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[F:5])([F:3])[F:2]

Participants

5

Reactant 3

HCID 6517TetraethoxysilaneHCID 6594ChlorotrifluoroethyleneHCID 178418400CID 53628100

Product 1

HCID 21864279Trifluorovinyl triethoxysilane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-80 °C

Procedure

200 ml of freshly distilled dry Et2O is added to a 500 ml vessel (under an argon atmosphere). The vessel is cooled down to −80° C. and 15 g (0.129 mol) of CF2═CFCl gas is bubbled to Et2O. 100 ml (0.13 mol) of sec-BuLi is added dropwise during three hours. The temperature of the solution is kept below −60° C. all the time. The solution is stirred for 15 minutes and 29 ml (27.08 g, 0.130 mol) of Si(OEt)4 is added in small portions. The solution is stirred for over night allowing it to warm up to room temperature. Formed red solution is filtered and evaporated to dryness to result crude trifluorovinyltriethoxysilane, CF2═CFSi(OEt)3.

Workup

  1. distillation200 ml of freshly distilled dry Et2O
  2. additionis added to a 500 ml vessel (under an argon atmosphere)
  3. customis kept below −60° C.
  4. stirringThe solution is stirred for over night
  5. temperatureto warm up to room temperature
  6. customFormed red solution
  7. filtrationis filtered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-8632e8ae6e9b4da791327f510e0f35d8
Source dataset
uspto-grants-2004_10
Patent number
US06803476B2

Reaction notes

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