反応 #607448

反応方程式

hex-5-enal

trimethyl(trifluoromethyl)silane

→

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

収率 31.0%

溶媒

THF

反応条件

後処理

1. 1
   その他The 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
   その他the layers were separated
5. 5
   抽出The aqueous fraction was additionally extracted with Et2O
6. 6
   洗浄the combined organic phases were washed sequentially with a saturated aqueous NaHCO3 solution, water, and brine
7. 7
   乾燥After drying with MgSO4 and filtration the solvent
8. 8
   その他was removed under reduced pressure
9. 9
   その他the 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
    その他were collected
12. 12
    濃縮concentrated in vacuo

実験手順

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.

出典