Silane, tris(1-methylethyl)- → HCID 131719393, compound

HRID 864616Notes

Reaction equation

HRID 864616 reaction equation
C([SiH](C(C)C)C(C)C)(C)C.[C:11]([CH2:15][O:16][C:17]([C:20]([C:23](Cl)=[O:24])([F:22])[F:21])([F:19])[F:18])([F:14])([F:13])[F:12]>[Pd]>[C:11]([CH2:15][O:16][C:17]([C:20]([CH:23]=[O:24])([F:22])[F:21])([F:19])[F:18])([F:14])([F:13])[F:12]

Participants

4

Reactant 2

HCID 138754Silane, tris(1-methylethyl)-HCID 131719394HCID 131719394, compound

Product 1

HCID 131719393HCID 131719393, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
0 °C

Procedure

A 3-necked round bottom flask was charged with 10% Pd/C (400 mg) and cooled to 0° C. Triisopropylsilane (6.44 g, 40.7 mmol) was added, and CF3CH2OCF2CF2COCl (9.15 g, 34.9 mmol) was added dropwise. The mixture was warmed to room temperature, and the exotherm was then controlled by a room temperature water bath. The mixture was stirred an additional 22 hr over which time an additional 0.2 g of catalyst was added. The product was removed by vacuum transfer at 27 Pa. After isolation of the lower layer and washing several times with petroleum ether at -25° C., there was obtained 4.32 g of colorless liquid. 19F NMR (glyme-d10): -74.4 (t of t'2, J=8.2, 2.7), -87.35 (m, OCF2), -128.27 (apparent quartet, J=4 Hz, CF2CHO). GC/MS showed the major product with a fragment ion of m/z=209.0023. Calcd. for C5H3F6O2 (M-F): 209.0037.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. customwas then controlled by a room temperature
  3. additionwas added
  4. customThe product was removed by vacuum transfer at 27 Pa
  5. washAfter isolation of the lower layer and washing several times with petroleum ether at -25° C.

Sources & evidence

ORD record
ord-23a8e6cfcd84456da088b4f7f0076628
Source dataset
uspto-grants-1996_10
Patent number
US05563235

Reaction notes

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