Ammonium Chloride → 2-Benzyl-3-(3-benzyloxy-4-nitrophenyl)-1-phenylpropan-1-one

Temperature

-78 °C

To a solution of 1,3 diphenylpropan-1-one (231 mg, 1.1 mmol) in THF (2.5 mL) at −78° C. is added dropwise LiHMDS (1M in THF, 1.3 mL), over a period of 15 min. The mixture is stirred at −78° C. for 30 min then a solution of 2-benzyloxy-4-bromomethyl-1-nitrobenzene (321 mg, 1 mmol) in THF (2.5 mL) is added over a period of 15 min. The mixture is stirred at −78° C. for 15 min, then allowed to slowly warm to RT and stirred there for 45 min. The mixture is diluted with EtOAc, cooled to −25° C. and a solution of saturated ammonium chloride is added dropwise. The organic phase is washed with saturated ammonium chloride and brine, dried over MgSO4, filtered and concentrated to afford crude product which is purified using flash chromatography to give the title compound as a gum.

1. stirringThe mixture is stirred at −78° C. for 15 min
2. temperatureto slowly warm to RT
3. stirringstirred there for 45 min
4. temperaturecooled to −25° C.
5. washThe organic phase is washed with saturated ammonium chloride and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customto afford crude product which
10. customis purified

ORD record

ord-e10ddec916b449c189cda98ce9fb9451

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084448B2