Sulfuric Acid → HCID 89851775, compound

Participants

Reaction Steps

To a solution of trifluoromethoxybenzene (5.29 mL) and N,N,N′,N′-tetramethylethylene-diamine (5.96 mL) in tetrahydrofuran (80 mL) at −78° C. was added sec-butyllithium (32 mL, 1.4 M solution) over 50 minutes. After 2 hours a cooled (−78° C.) solution (R)-(+)-propylene oxide (4.20 mL) in tetrahydrofuran (20 mL) was added over 15 minutes, followed by boron trifluoride diethyl etherate (1.89 mL) over 20 minutes. The reaction mixture was stirred at −78° C. for 2 hours after which aqueous solution of H2SO4 (0.3 M, 50 mL) and water (10 mL) was added. The mixture let to warm up to room temperature after which it was extracted with diethyl ether (2×100 mL). The combined organic phases were washed with brine, dried with Na2SO4 and concentrated. Evaporation residue was purified by separation method E (ethyl acetate-heptane). (Yield 1.40 g).

Provenance & Evidence