Reaction #607448

Reaction equation

hex-5-enal

trimethyl(trifluoromethyl)silane

→

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

Yield 31.0%

Solvents

THF

Conditions

Workup

1. 1
   OtherThe 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
   Otherthe layers were separated
5. 5
   ExtractionThe aqueous fraction was additionally extracted with Et2O
6. 6
   Washthe combined organic phases were washed sequentially with a saturated aqueous NaHCO3 solution, water, and brine
7. 7
   DryingAfter drying with MgSO4 and filtration the solvent
8. 8
   Otherwas removed under reduced pressure
9. 9
   Otherthe 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
    Otherwere collected
12. 12
    Concentrationconcentrated in vacuo

Procedure

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.

Source