Réaction #2158

Équation de réaction

α,α,α-trifluoro-o-tolualdehyde

iodochloromethane

methyllithium

→

oil

2-(2-Trifluoromethyl-phenyl)oxirane

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONadded over 5 minutes
2. 2
   workup.WAITThe reaction was left
3. 3
   Températureto warm up to room temperature overnight
4. 4
   AutreThe reaction was quenched
5. 5
   Extractionextracted
6. 6
   LavageThe combined organic extracts were washed with brine
7. 7
   Séchagedried (MgSO4)
8. 8
   Concentrationconcentrated
9. 9
   Autreto afford a brown oil
10. 10
    AutrePurification on flash silica
11. 11
    Lavageeluted with 100% hexane up to 5% EtOAC in hexane

Mode opératoire

α,α,α-trifluoro-o-tolualdehyde (3 g) was dissolved in anhydrous tetrahydrofuran and cooled to -78° C., iodochloromethane (1.38 ml) was then added, followed by methyllithium (1.5M complexed with lithium bromide) (12 ml) added over 5 minutes. The reaction was left to warm up to room temperature overnight. The reaction was quenched using saturated ammonium chloride solution and extracted using diethyl ether (2×50 ml). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to afford a brown oil. Purification on flash silica eluted with 100% hexane up to 5% EtOAC in hexane afforded a colourless oil (1.1 g). 1H NMR (250 MHz, CDCl3) δ2.61-2.71 (1H, dd), 3.14-3.25 (1H, dd), 4.17-4.27 (1H, m), 7.33-7.70 (5H, m).

Source