Method for synthesizing 2-benzylidene tetrahydrothiophene derivative
a tetrahydrothiophene and tetrahydrothiophene technology, applied in the field of organic synthesis, can solve the problems of complex raw material preparation, expensive metal catalysts, etc., and achieve the effect of convenient post-treatment and simple reaction conditions
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example 1
Synthesis of 2-benzylidene tetrahydrothiophene
[0029](Cyclopropylethynyl)benzene (compound corresponding to No. (1), 0.0711 g, 0.5 mmol) and sodium sulfide nonahydrate (0.2402 g, 1.0 mmol) were weighed and fed to a 25 mL reaction tube. DMA (2.5 mL) was added as a solvent, and the reaction was performed under stirring for 9 hrs at 150° C. After the reaction, the reaction solution was extracted with ethyl acetate and saturated brine, dried over anhydrous sodium sulfate and filtered with suction. The resulting filtrate was rotary evaporated to dryness, the sample was loaded, and separated by column chromatography (conditions: stationary phase 300-400-mesh silica gel powder, and mobile phase petroleum ether) to afford a reaction product (0.0608 g).
[0030]The reaction product was characterized. The results are shown below:
[0031]1H NMR (400 MHz, CDCl3) δ=7.42 (d, J=7.3 Hz, 1H), 7.35-7.24 (m, 2H), 7.24-7.10 (m, 1H), 6.46 (s, 0.76×1H), 6.42 (t, J=1.9 Hz, 0.24×1H), 3.14 (t, J=6.4 Hz, 0.76×2H),...
example 2
Synthesis of 2-(4-chlorobenzylidene)tetrahydrothiophene
[0033]1-chloro-4-(cyclopropylethynyl)benzene (compound corresponding to No. (2), 0.0883 g, 0.5 mmol) and sodium sulfide nonahydrate (0.2402 g, 1.0 mmol) were weighed and fed to a 25 mL reaction tube. DMA (2.5 mL) was added as a solvent, and the reaction was performed under stirring for 12 hrs at 150° C. After the reaction, the reaction solution was extracted with ethyl acetate and saturated brine, dried over anhydrous sodium sulfate and filtered with suction. The resulting filtrate was rotary evaporated to dryness, the sample was loaded, and separated by column chromatography (conditions: stationary phase 300-400-mesh silica gel powder, and mobile phase petroleum ether) to afford a reaction product (0.0759 g).
[0034]The reaction product was characterized. The results are shown below:
[0035]1H NMR (400 MHz, CDCl3) δ=7.40-7.31 (m, 2H), 7.31-7.25 (m, 2H), 6.41 (s, 0.95×1H), 6.36 (s, 0.05×1H), 3.19 (t, J=6.4 Hz, 0.95×2H), 3.07 (t, J=6...
example 3
Synthesis of 2-(4-bromobenzylidene)tetrahydrothiophene
[0037]1-bromo-4-(cyclopropylethynyl)benzene (compound corresponding to No. (3), 0.1105 g, 0.5 mmol) and sodium sulfide nonahydrate (0.2402 g, 1.0 mmol) were weighed and fed to a 25 mL reaction tube. DMA (2.5 mL) was added as a solvent, and the reaction was performed under stirring for 12 hrs at 150° C. After the reaction, the reaction solution was extracted with ethyl acetate and saturated brine, dried over anhydrous sodium sulfate and filtered with suction. The resulting filtrate was rotary evaporated to dryness, the sample was loaded, and separated by column chromatography (conditions: stationary phase 300-400-mesh silica gel powder, and mobile phase petroleum ether) to afford a reaction product (0.0842 g).
[0038]The reaction product was characterized. The results are shown below:
[0039]1H NMR (400 MHz, CDCl3) δ=7.48-7.38 (m), 7.32-7.27 (m), 7.12-7.04 (m), 6.41 (s, 0.77×1H), 6.36 (t, J=2.0 Hz, 0.23×1H), 3.20 (t, J=6.4 Hz, 0.77×2H...
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