Method for preparing a 2, 3-dihydrofuran derivative
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A kind of technology of dihydrofuran and derivatives, applied in the field of organic synthesis
Pending Publication Date: 2021-07-30
HUAIHUA UNIV
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Embodiment 1
[0030]
[0031] In the Schlenk bottle, add the compound (55.6mg, 0.2mmol) shown in formula 1a, the nitrile compound (0.2mL) shown in formula 2a, H 2 O (1.8mL), tert-butyl peroxybenzoate (TBPB, 77.7mg, 2.0eq), then the reactor was stirred and reacted at 130°C under an air atmosphere, and the reaction process was monitored by TLC until the raw materials disappeared (the reaction time was 12 hours), after the reaction was completed, the reaction solution was extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent, and the residue was separated by column chromatography (elution solvent: ethyl acetate / n-hexane) to obtain target product I-1 (83%yield); 1 H NMR (500MHz, CDCl 3 )δ:7.43-7.41(m,2H),7.24-7.21(m,1H),7.19-7.17(m,3H),7.09-7.04(m,4H),3.19-3.10(m,2H),2.60- 2.56(m,2H),2.26-2.16(m,2H),1.59(s,3H); 13 C NMR (125MHz, CDCl 3 )δ: 193.4, 164.3, 138.8, 131.3, 130.9, 130.2, 1...
Embodiment 2
[0033] The reaction temperature was lowered to 120° C. for the reaction, and the remaining conditions were the same as in Example 1, and the yield of the target product I-1 was 65%.
Embodiment 3
[0035] The oxidizing agent used dibenzoyl peroxide (BPO) instead of tert-butyl peroxybenzoate (TBPB), and the remaining conditions were the same as in Example 1, and the yield of the target product I-1 was 61%.
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Abstract
The invention discloses a method for preparing a 2, 3-dihydrofuran derivative through a nitrile C (sp3)-H functionalization initiated alkenyl-1, 3-dicarbonyl compound free radical cyclization reaction under a metal-free and alkali-free water phase system. The method comprises the following steps: adding an alkenyl-1, 3-dicarbonyl compound, a nitrile compound, an oxidizing agent and water into a Schlenk reaction flask, and stirring and reacting at a certain temperature in an air atmosphere to obtain the 2, 3-dihydrofuran derivative.
Description
technical field [0001] The application belongs to the field of organic synthesis, in particular to nitrile C (sp) under a metal-free and alkali-free aqueous phase system 3 A green method for the preparation of 2,3-dihydrofuran derivatives by free radical cyclization of alkenyl-1,3-dicarbonyl compounds initiated by )-H functionalization. Background technique [0002] In modern synthetic chemistry, since solvents account for more than half of the total materials in the reaction process, the development of environmentally friendly and green reaction media remains an important goal. Organic transformations in aqueous solutions have attracted much attention due to the wide variety of sources, redox stability, non-toxicity, safety, and ease of product separation. Meanwhile, the metal-free strategy provides a good platform for pursuing green and sustainable chemistry, which does not require expensive transition metal catalysts or ligands, and has no metal residues in the final pro...
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