Synthesis method of monosubstituted or disubstituted furan derivatives
A technology of furan derivatives and synthetic methods, which is applied in the field of pharmaceutical synthesis, and achieves the effects of simple steps, mild reaction conditions and high reaction yield
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Embodiment 1
[0037] Synthesis
[0038] 5-Hydroxymethyl-3-p-tolyl-Δ 2 - To a solution of isoxazoline (0.4 mmol) in acetic acid-water (3:1, 8 mL) was added zinc powder (2.0 mmol). After the addition was complete, the reaction temperature was raised to 100°C and stirred for 3 hours. The reaction solution was cooled to room temperature and diluted with water. Ethyl acetate was added to extract the product. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined and washed with water and saturated sodium carbonate solution three times respectively, dried by adding magnesium sulfate, filtered, and the filtrate was evaporated to remove the solvent on a rotary evaporator under reduced pressure. The residue was purified by silica gel column chromatography (washed with petroleum ether) to obtain the product 2-p-tolylfuran with a yield of 93%. The NMR data are as follows: 1 H NMR (300MHz, CDCl3) δ7.60 (2H, d, J = 8.2Hz), ...
Embodiment 2
[0040] Synthesis
[0041] 5-Hydroxymethyl-3-p-methoxyphenyl-Δ 2 - Iron powder (2.0 mmol) was added to a solution of isoxazoline (0.4 mmol) in acetic acid-water (3:1, 8 mL). After the addition was complete, the reaction temperature was raised to 100°C and stirred for 2 hours. The reaction solution was cooled to room temperature and diluted with water. Ethyl acetate was added to extract the product. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined and washed with water and saturated sodium carbonate solution three times respectively, dried by adding magnesium sulfate, filtered, and the filtrate was evaporated to remove the solvent on a rotary evaporator under reduced pressure. The residue was purified by silica gel column chromatography (washed with petroleum ether) to obtain the product 2-p-methoxyphenylfuran with a yield of 85%. The NMR data are as follows: 1 H NMR (300MHz, CDCl 3 )δ7.6l (2...
Embodiment 3
[0043] Synthesis
[0044] 3-p-fluorophenyl-5-hydroxymethyl-Δ 2- To a solution of isoxazoline (0.4 mmol) in dilute hydrochloric acid (0.2M, 8 mL) was added zinc powder (2.0 mmol). After the addition was complete, the reaction temperature was raised to 100°C and stirred for 3 hours. The reaction solution was cooled to room temperature and diluted with water. Ethyl acetate was added to extract the product. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined and washed with water and saturated sodium carbonate solution three times respectively, dried by adding magnesium sulfate, filtered, and the filtrate was evaporated to remove the solvent on a rotary evaporator under reduced pressure. The residue was purified by silica gel column chromatography (washed with petroleum ether) to obtain the product 2-fluorophenylfuran with a yield of 65%. The NMR data are as follows: 1 H NMR (300MHz, CDCl 3 )δ7.62...
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