Triacetoxyperiodinane → 1-(5-Chloropyridin-2-yl)-2,2,2-trifluoroethanone

To a solution of 1-(5-chloropyridin-2-yl)-2,2,2-trifluoroethanol (0.643 g, 3.04 mmol) in DCM (9 mL) at 0° C. was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (1.55 g, 3.65 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 20 h before quenching with saturated NaHCO3 (10 mL) and saturated sodium thiosulfate solution. The reaction mixture was stirred for 20 min and transferred to a separatory funnel. The aqueous phase was discarded and the organic phase was washed with brine and dried over MgSO4 The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (5% to 30% EtOAc in heptane) to afford the title compound (0.545 g, 2.60 mmol, 86% yield) as a pale yellow oil. LC/MS (ESI+) m/z=209.9 (M+H).

1. custombefore quenching with saturated NaHCO3 (10 mL) and saturated sodium thiosulfate solution
2. stirringThe reaction mixture was stirred for 20 min
3. customtransferred to a separatory funnel
4. washthe organic phase was washed with brine
5. dry with materialdried over MgSO4 The filtrate
6. concentrationwas concentrated under reduced pressure
7. customthe residue was purified by flash column chromatography on silica gel (5% to 30% EtOAc in heptane)

ORD record

ord-c3d93f2e02784a6cbd887f5d7b9874f5

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2