Reacción #607448

Ecuación de reacción

hex-5-enal

trimethyl(trifluoromethyl)silane

→

1,1,1-trifluorohept-6-en-2-ol

Rendimiento 31.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe ice bath was removed
2. 2
   workup.ADDITIONUpon complete transformation of the starting material the reaction mixture was treated with 2M HCl
3. 3
   workup.ADDITIONThen, 50 mL of Et2O was introduced
4. 4
   Otrothe layers were separated
5. 5
   ExtracciónThe aqueous fraction was additionally extracted with Et2O
6. 6
   Lavadothe combined organic phases were washed sequentially with a saturated aqueous NaHCO3 solution, water, and brine
7. 7
   SecadoAfter drying with MgSO4 and filtration the solvent
8. 8
   Otrowas removed under reduced pressure
9. 9
   Otrothe resultant crude residue was purified by column chromatography (silica gel, pentane/Et2O, v/v=8/2)
10. 10
    workup.ADDITIONFractions containing the pure compound
11. 11
    Otrowere collected
12. 12
    Concentraciónconcentrated in vacuo

Procedimiento

To a ice-bath cooled solution of hex-5-enal (500 mg, 4.331 mmol) and trimethyl(trifluoromethyl)silane (0.74 g, 5.13 mmol, 1.2 equiv.) in THF (10 mL) was added tetrabutylammonium hydrofluoride (10 mg, 0.04 mmol). The ice bath was removed and the reaction progress was monitored via GCMS and 1H NMR. Upon complete transformation of the starting material the reaction mixture was treated with 2M HCl and stirred for an additional 2 h. Then, 50 mL of Et2O was introduced and the layers were separated. The aqueous fraction was additionally extracted with Et2O and the combined organic phases were washed sequentially with a saturated aqueous NaHCO3 solution, water, and brine. After drying with MgSO4 and filtration the solvent was removed under reduced pressure and the resultant crude residue was purified by column chromatography (silica gel, pentane/Et2O, v/v=8/2). Fractions containing the pure compound were collected and concentrated in vacuo to give 1,1,1-trifluorohept-6-en-2-ol (225 mg, 31% yield) as a yellow oil.

Fuente