Pyridine → 4-Chloromethyl-4-methyl-oxazolidin-2-one

To a suspension of 4-(hydroxymethyl)-4-methyloxazolidin-2-one (1.89 g, 14.4 mmol) in 1,2-dichloroethane (10 ml) was added thionyl chloride (5.0 ml, 69 mmol). The solution was stirred for 30 min at RT, and then pyridine (5.0 ml, 62 mmol) was added. The solution was heated to 90° C. for 16 h and then 110° C. for an additional 2 h, then cooled to RT and evaporated. The residue was purified by flash chromatography (30% to 100% ethyl acetate in hexanes, Rf=0.25 in 1:1 ethyl acetate:hexanes) to give the title compound as a clear oil which solidified to a white solid upon standing (1.52 g, 10.2 mmol, 71%). 1H NMR (CDCl3, 400 MHz) δ 1.49 (s, 3H), 3.55 (m, 2H), 4.12 (d, 1H, J=9.2 Hz), 4.31 (d, 1H, J=8.8 Hz), 5.4 (br s, 1H). LRMS (ESI/APCI): 150 [M+H]+.

1. temperatureThe solution was heated to 90° C. for 16 h
2. wait110° C. for an additional 2 h
3. temperaturecooled to RT
4. customevaporated
5. customThe residue was purified by flash chromatography (30% to 100% ethyl acetate in hexanes, Rf=0.25 in 1:1 ethyl acetate:hexanes)

ORD record

ord-df8cc368f71a48e8a29d2e1cb4473c3d

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729112B2