Potassium Hydroxide → HCID 67500957, compound

Participants

Reaction Steps

To a stirred and cooled (0° C.) solution of KOH (0.26 g, 3.92 mmol) in MeOH (36 mL) was added successively 4-fluorobenzaldehyde (0.443 g, 3.56 mmol) and N,N-diethyl-2-isocyanoacetamide (0.50 g, 3.57 mmol). The solution was stirred for 16 h (0° C. to RT) and then concentrated. The residue was partitioned between CH2Cl2 (20 mL) and brine (20 mL). The organic layer was separated and the desired product was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine (30 mL), dried over MgSO4, filtered and evaporated. A pale crude yellow solid was obtained the (±)-trans-N,N-diethyl-5-(4-fluorophenyl)-4,5-dihydrooxazole-4-carboxamide, SLA 19142, as a brown oil (0.86 g, 91% yield).

Provenance & Evidence