Реакция #607448

Уравнение реакции

hex-5-enal

trimethyl(trifluoromethyl)silane

→

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

Выход 31.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   ДругоеThe 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
   Другоеthe layers were separated
5. 5
   ЭкстракцияThe aqueous fraction was additionally extracted with Et2O
6. 6
   Промывкаthe combined organic phases were washed sequentially with a saturated aqueous NaHCO3 solution, water, and brine
7. 7
   СушкаAfter drying with MgSO4 and filtration the solvent
8. 8
   Другоеwas removed under reduced pressure
9. 9
   Другоеthe 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
    Другоеwere collected
12. 12
    Концентрированиеconcentrated in vacuo

Методика

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.

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