Organic reactions without an organic medium . Utilization of perfluorotriethylamine as a reaction medium

Abstract

Perfluorotriethylamine is a good alternative reaction medium for Lewis acid catalyzed reactions and it can be easily recycled by simple extractive workup.

References

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9. Typical procedure is as follows. Under a nitrogen atmosphere, titanium tetrachloride (0.220 ml, 2 mmol) was added dropwise to aldehyde (2 mmol) and allyltrimethylsilane (0.333 ml, 2.1 ml) in perfluorotriethylamine (4 ml) at –78 °C. After completion of the addition, the dry ice-acetone bath was removed and the reaction mixture was stirred for 15 min at rt. The reaction was quenched with 4 ml of water, and stirred for a few minutes. Then, 3.6 ml of fluorous solvent was recovered by three phase extraction (organic layer: 4 ml of ethyl acetate). The organic layer was dried over anhydrous Na₂SO₄ and concentrated in vacuo. Purification of the residue by silica gel chromatography afforded the homoallyl alcohol.