Water → Methyl 2-phenoxythiazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of commercially available methyl 2-bromothiazole-4-carboxylate (1.000 g; 4.50 mmol) and sodium phenoxide (627 mg; 5.40 mmol) in anh. DMSO (20 ml) was heated to 80° C., under nitrogen, for 17 h. A second addition of sodium phenoxide (314 mg; 2.70 mmol) was performed, and the resulting mixture was further heated at 80° C. for 1 h. After cooling to rt, water (50 ml), brine (10 ml), and toluene (20 ml) were added. The separated aq. layer was further extracted with toluene (2×20 ml). The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=50/1) afforded methyl 2-phenoxythiazole-4-carboxylate as a yellow oil. LC-MS (conditions A): tR=0.73 min.; [M+H]+: 236.06 g/mol.

Provenance & Evidence