Triacetoxyperiodinane → 1-(4-Bromopyridin-2-yl)ethan-1-one

To a stirring solution of 1-(4-bromopyridin-2-yl)ethanol (2.93 g, 14.5 mmol) in DCM (50 mL) was added Dess-Martin periodinane (12.93 g, 30.5 mmol) portion-wise over several minutes. The reaction was then quenched with saturated 1:1 Na2S2O3/NaHCO3 solution (200 mL) and stirred until gas evolution ceased. The aqueous layer was extracted with DCM, dried over MgSO4, and purified by column chromatography (gradient 0 to 10% EtOAc in hexanes) to give the product. 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=5.2 Hz, 1H), 8.20 (d, J=1.9 Hz, 1H), 7.64 (dd, J=5.2, 1.9 Hz, 1H), 2.71 (s, 3H).

1. customThe reaction was then quenched with saturated 1:1 Na2S2O3/NaHCO3 solution (200 mL)
2. extractionThe aqueous layer was extracted with DCM
3. dry with materialdried over MgSO4
4. custompurified by column chromatography (gradient 0 to 10% EtOAc in hexanes)
5. customto give the product

ORD 기록

ord-68b42f2e4d0d41a5b792c058d3ce98e3

출처 데이터셋

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08987250B2