1,2,4-trisubstituent furan compound and preparation method thereof
A compound and three-substitution technology, applied in the field of synthesis of furan derivatives, can solve the problems of harsh reaction conditions, troublesome operation, difficult preparation of starting materials, etc., and achieve the effect of simple reaction conditions and convenient preparation
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Embodiment 1
[0010]
[0011] Into a 10 mL round bottom flask was added 2 mL of toluene, ethyl 2-chloroacetoacetate (1.1 mmol, 181 mg), triphenylphosphine (PPh 3 ) (0.5 mmol, 131 mg), stirred at room temperature for 5 min, then added 1a (1 mmol, 144 mg) and potassium carbonate (1 mmol, 138 mg), stirred at room temperature for 1.5 hours, then added 2 mL of saturated ammonium chloride solution to quench the reaction, Extracted with ethyl acetate (5 mL×3), washed with saturated brine, dried over anhydrous sodium sulfate, filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=30 / 1) to obtain the yellow oily product 2- Ethyl methyl-5-(2-oxo-2-phenethyl)furan-3-carboxylate 2a (177 mg, 65%). The characterization data of this compound are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 7.982 (d, J = 8.0 Hz, 2H), 7.569 (t, J = 7.2 Hz, 1H), 7.459 (t, J = 8.0 Hz, 1H), 6.493 (s, 1H), 4.242 (s, 2H ), 4.239 (q, J = 7.6 Hz, 2H), 2.523 (s, 3H), 1.302 (t, J = 7.6 Hz, 3H); 1...
Embodiment 2
[0013]
[0014] Into a 10 mL round bottom flask was added 2 mL of toluene, ethyl 2-chloroacetoacetate (1.1 mmol, 181 mg), triphenylphosphine (PPh 3 ) (0.5 mmol, 131 mg), stirred at room temperature for 5 min, then added 1b (1 mmol, 162 mg) and potassium carbonate (1 mmol, 138 mg), stirred at room temperature for 1.5 hours, then added 2 mL of saturated ammonium chloride solution to quench the reaction, Extracted with ethyl acetate (5 mL×3), washed with saturated brine, dried over anhydrous sodium sulfate, filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate = 30 / 1) to obtain the yellow solid product 2- Ethyl methyl-5-(2-oxo-2-(4-fluorophenyl)ethyl)furan-3-carboxylate 2b (168mg, 58%). The characterization data of this compound are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 8.030-7.995 (m, 2H), 7.313-7.308 (m, 1H), 7.149-7.106 (m, 2H), 6.485 (s, 1H), 4.239 (q, J = 7.6 Hz, 2H), 4.213 ( s, 2H), 2.520 (s, 3H), 1.302 (t, J = 7.2 Hz, 3H); 13 C NMR ...
Embodiment 3
[0016]
[0017] Into a 10 mL round bottom flask was added 2 mL of toluene, ethyl 2-chloroacetoacetate (1.1 mmol, 181 mg), triphenylphosphine (PPh 3 ) (0.5 mmol, 131 mg), stirred at room temperature for 5 min, then added 1c (1 mmol, 178 mg) and potassium carbonate (1 mmol, 138 mg), stirred at room temperature for 1.5 hours, then added 2 mL of saturated ammonium chloride solution to quench the reaction, Extracted with ethyl acetate (5 mL×3), washed with saturated brine, dried over anhydrous sodium sulfate, filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate = 30 / 1) to obtain the yellow solid product 2- Ethyl methyl-5-(2-oxo-2-(4-chlorophenyl)ethyl)furan-3-carboxylate 2c (159 mg, 52%). The characterization data of this compound are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 7.925 (d, J = 8.8 Hz, 2H), 7.437 (d, J = 8.8 Hz, 2H), 6.487 (s, 1H), 4.244 (q, J = 7.2 Hz, 2H), 4.216 (s, 2H ), 2.524 (s, 3H), 1.308 (t, J = 6.8 Hz, 3H); 13 C NMR (100 MHz...
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