Sodium hydride → 2-[3,5-Bis(trifluoromethyl)phenyl]oxirane

In a dry flask was placed NaH (1.09 g of 60% NaH, 27.27 mmol). DMSO (90 mL) was added followed by trimethylsulfoxonium iodide (7.0 g, 31.82 mmol). The reaction was stirred for 5 minutes and then 3,5-bis(trifluoromethyl)benzaldehyde (1.5 mL, 9.09 mmol) was added as a solution in DMSO (15 mL). The reaction was stirred at room temperature for 1 hour and then poured into ice/water (300 mL). The mixture was extracted with pentanes (3×150 mL). The pentane extracts were combined and filtered through a short plug of silica gel with 10% Et2O/pentanes. The filtrate was concentrated and the residue was purified by flash chromatography with 10% Et2O/pentanes to give 2-[3,5-bis(trifluoromethyl)phenyl]oxirane. Rf=0.42 (10% Et2O/pentanes). 1H NMR (CDCl3, 500 MHz) 7.82 (s, 1H), 7.74 (s, 2H), 3.99 (dd, J=3.9, 2.5 Hz, 1H), 3.23 (dd, J=5.2, 4.1 Hz, 1H), 2.79 (dd, J=5.5, 2.5 Hz, 1H).

1. customIn a dry flask was placed
2. stirringThe reaction was stirred at room temperature for 1 hour
3. extractionThe mixture was extracted with pentanes (3×150 mL)
4. filtrationfiltered through a short plug of silica gel with 10% Et2O/pentanes
5. concentrationThe filtrate was concentrated
6. customthe residue was purified by flash chromatography with 10% Et2O/pentanes

ORD record

ord-2f181eb311f6473ca600e7417016e5f7

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07652049B2