methyl 5-methylbenzo[d]oxazole-2-carboxylate synthesis
- Product Name:methyl 5-methylbenzo[d]oxazole-2-carboxylate
- CAS Number:27383-91-1
- Molecular formula:C10H9NO3
- Molecular Weight:191.18
10531-78-9
124-38-9
74-88-4
27383-91-1
Catalyst (9.9 mg, 0.025 mmol, 5 mol%), potassium tert-butoxide (0.0672 g, 0.6 mmol) and DMF (3.0 mL) were added to the reaction flask under argon protection. Subsequently, 5-methylbenzazole (66.58 mg, 0.5 mmol) was added and the reaction mixture was stirred at 80 °C for 18 h at atmospheric pressure. After completion of the reaction, the system was cooled to 65 °C, iodomethane (93 μL, 1.5 mmol) was added and stirring was continued for 1 h at the same temperature. At the end of the reaction, the reaction was quenched with ethyl acetate and purified by column chromatography (eluent: ethyl acetate/petroleum ether, 1:10, v/v) to afford the target product methyl 5-methylbenzo[D]oxazole-2-carboxylate in 88% yield.
10531-78-9
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Yield:27383-91-1 89.9%
Reaction Conditions:
Stage #1: 5-methyl-1,3-benzoxazole;carbon dioxidewith Mo2(O-t-Bu)6;caesium carbonate in N,N-dimethyl-formamide at 75; under 760.051 Torr; for 10 h;Schlenk technique;
Stage #2: methyl iodide in N,N-dimethyl-formamide at 50; for 2 h;Schlenk technique;
References:
Chen, Jing-Huo;Deng, Cheng-Hua;Fang, Sheng;Ma, Jian-Gong;Cheng, Peng [Green Chemistry,2018,vol. 20,# 5,p. 989 - 996]
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27383-91-1
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