3-METHYL-ISOCHROMEN-1-ONE synthesis
- Product Name:3-METHYL-ISOCHROMEN-1-ONE
- CAS Number:29539-21-7
- Molecular formula:C10H8O2
- Molecular Weight:160.1693
Yield:29539-21-7 92%
Reaction Conditions:
with potassium carbonate in dimethyl sulfoxide at 100; for 2 h;Inert atmosphere;Sealed tube;Reagent/catalyst;Solvent;Temperature;Time;
Steps:
Typical procedure for copper nanoparticles catalyzed synthesis of 3-substituted isocoumarins from 2-chlorobenzoic acids and pentane-2,4-dione (entry 2, Table 1)
2-chlorobenzoic acids (1a, 0.2 mmol), pentane-2,4-dione (2a, 2 eq), Cu NPs (1.3 mg, 10 mol%), K2CO3 (2.0 equiv) and 1.5 mL of DMSO were added into a 5-mL sealed tube under N2. The mixture was stirred at 100 °C for 2 h. The reaction mixture was then purified by flash column chromatography on silica gel (hexanes/EtOAc 15:1). Compound 3a was obtained in >92% of yield. 3-methyl-1H-isochromen-1-one (3a). 1H NMR (400 MHz, CDCl3, ppm) δ 8.25 (d, J = 8.0 Hz, 1H), 7.67 (t, J = 8.2 Hz, 1H), 7.45 (t, J = 8.0 Hz, 1H), 7.34 (d, J = 7.9 Hz, 1H), 6.26 (s, 1H), 2.29 (s, 3H); 13C NMR (101 MHz, CDCl3, ppm) δ 163.0, 154.6, 137.7, 134.8, 129.5, 127.6, 124.9, 120.0, 103.6, 19.7 (Ref. 10). The characterization data for all of products were also provided in SI, 1H & 13C NMR Spectrum were also attached.
References:
Wang, Xiaowen;Wu, Chaolong;Sun, Youwen;Yao, Xiaoquan [Tetrahedron Letters,2017,vol. 58,# 32,p. 3164 - 3167] Location in patent:supporting information
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