Ethyl Acetate → Methyl 2-thiomorpholinobenzoxazole-4-carboxylate

Participants

Reaction Steps

A solution of methyl 2-chlorobenzoxazole-4-carboxylate (1.0 g, 4.7 mmol) and thiomorpholine (1.4 mL, 14 mmol) in THF (20 mL) was stirred at ambient temperature for 1 h. Then, the reaction mixture was poured into EtOAc (100 mL) and washed with 1N HCl (20 mL), H2O (20 mL), brine (20 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (silica gel, 5 to 50% EtOAc in hexanes) gave methyl 2-thiomorpholinobenzoxazole-4-carboxylate (1.1 g, 84%) as a yellow solid. 1H NMR and MS consistent.

Provenance & Evidence