Ethyl Acetate → HCID 86665537, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (10.22 g, 68.32 mmol) in N,N-dimethylformamide (100 ml) was added potassium thioacetate (9.07 g, 79.6 mmol). The suspension was heated to 90° C. for 18 hour, cooled to room temperature, and concentrated in vacuo. The residue was suspended in 400 ml ethyl acetate, washed three times with 100 ml saturated NaHCO3, 100 ml saturated NaCl, dried on MgSO4, and concentrated in vacuo. Flash chromatography (30% to 100% ethyl acetate in hexanes) afforded the title compound as a yellow oil (6.07 g, 31.2 mmol, 46%). 1H NMR (CDCl3, 400 MHz) δ 1.45 (s, 3H), 2.42 (s, 3H), 3.07 (d, J=14.0 Hz, 1H), 3.21 (d, J=14.0 Hz, 1H), 4.08 (d, J=8.8 Hz, 1H), 4.15 (d, J=8.8 Hz, 1H), 5.59 (br s, 1H); LRMS (ESI/APCI) m/z 190 [M+H]+.

Provenance & Evidence