2-[2-(trifluoromethyl)phenyl]oxirane

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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). added over 5 minutes The reaction was left to warm up to room temperature overnight The reaction was quenched extracted The combined organic extracts were washed with brine dried (MgSO4) concentrated to afford a brown oil Purification on flash silica eluted with 100% hexane up to 5% EtOAC in hexane

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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). added over 5 minutes The reaction was left to warm up to room temperature overnight The reaction was quenched extracted The combined organic extracts were washed with brine dried (MgSO4) concentrated to afford a brown oil Purification on flash silica eluted with 100% hexane up to 5% EtOAC in hexane

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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). added over 5 minutes The reaction was left to warm up to room temperature overnight The reaction was quenched extracted The combined organic extracts were washed with brine dried (MgSO4) concentrated to afford a brown oil Purification on flash silica eluted with 100% hexane up to 5% EtOAC in hexane