Sulfuric Acid → HCID 89851775, compound

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).

1. additionwas added over 15 minutes
2. additionwas added
3. extractionwas extracted with diethyl ether (2×100 mL)
4. washThe combined organic phases were washed with brine
5. dry with materialdried with Na2SO4
6. concentrationconcentrated
7. customEvaporation residue
8. customwas purified by separation method E (ethyl acetate-heptane)

ORD record

ord-184bb035a6064b87b4c82eabc2fa20f4

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249127B2