Heptane → HCID 57470641, compound

HRID 855474Notes

Reaction equation

HRID 855474 reaction equation
[C:1]([O:4][C:5]([C:7]([F:10])([F:9])[F:8])=[CH2:6])(=[O:3])[CH3:2].[Cl:11][SiH:12]([Cl:14])[Cl:13].CCCCCCC>C1(C)C(C)=CC=CC=1>[C:1]([O:4][CH:5]([C:7]([F:10])([F:9])[F:8])[CH2:6][Si:12]([Cl:14])([Cl:13])[Cl:11])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8900HeptaneHCID 24811Trichlorosilane3×HCID 752541-Propen-2-ol, 3,3,3-trifluoro-, 2-acetate

Product 1

HCID 57470641HCID 57470641, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1-(Trifluoromethyl)ethenyl acetate (Aldrich, 188.0 grams, 1.22 mole), trichlorosilane (80.6 grams, 0.60 mole), and 200 ml heptane were placed in a round bottom flask equipped with a water condenser and nitrogen inlet. Platinum(O)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex in xylene (10 ml) was added to this solution and heated to reflux for 18 hours. Afterwards, the solution was cooled to room temperature and additional portions of trichlorosilane (80.6 grams, 0.60 mole) and platinum complex (5 ml) were added and heated to reflux for 48 hours. Proton NMR of the solution indicated about 75% conversion. A third portion of trichlorosilane (67.7 grams, 0.50 mole) and platinum complex (5 ml) were then added and the solution heated to reflux for 48 hours. Solvents were distilled off at atmospheric pressure and the residue was fractionally distilled under reduced pressure. 2-Acetoxy-3,3,3-trifluoropropyltrichlorosilane (251.7 grams) (1.A) was collected between 100–125° C. at 20 mm pressure as a clear liquid.

Workup

  1. customequipped with a water condenser and nitrogen inlet
  2. temperatureheated
  3. temperatureto reflux for 18 hours
  4. temperatureheated
  5. temperatureto reflux for 48 hours
  6. temperaturethe solution heated
  7. temperatureto reflux for 48 hours
  8. distillationSolvents were distilled off at atmospheric pressure
  9. distillationthe residue was fractionally distilled under reduced pressure
  10. custom2-Acetoxy-3,3,3-trifluoropropyltrichlorosilane (251.7 grams) (1.A) was collected between 100–125° C. at 20 mm pressure as a clear liquid

Sources & evidence

ORD record
ord-81b89901740847a6af3cbd2fa2795be1
Source dataset
uspto-grants-2007_08
Patent number
US07261992B2

Reaction notes

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