Ring-opening dichlorination reaction method of cyclopropenone and oxygen heterocyclic compound
A technology for cyclopropenone and chlorination reaction, which is applied in the field of ring-opening double chlorination reaction of cyclopropenone and oxygen heterocyclic compounds, can solve the problems of harsh synthesis reaction conditions and high cost, and achieve high yield of target products and easy Operation, the effect of excellent gram-level reactivity
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Embodiment 1-20
[0026] Embodiment 1-20 reaction condition optimization test
[0027] Using cyclopropenone and tetrahydrofuran shown in formula 1a as raw materials, the influence of different reaction conditions on the yield of target product 3b was explored, and representative examples 1-20 were selected, and the results are shown in Table 1. The reaction formula is as follows:
[0028]
[0029] Table 1:
[0030]
[0031]
[0032] b Indicates that the reaction was carried out under nitrogen atmosphere.
[0033] Taking Example 20 as an example, the typical reaction operation is as follows:
[0034] Cyclopropenone 1a (0.2mmol, 1.0 equivalent), CuCl 2 (0.4mmol, 2.0 equivalents), AlCl 3(0.06mmol), tetrahydrofuran (0.3mmol, 1.5 equivalents) and CH 3 CN (2 mL) was loaded into a 10 mL reaction tube. The reaction mixture was then stirred at 120° C. for 10 hours under nitrogen atmosphere. After the reaction was completed, 2.0ml of water was added to the reaction mixture, the reaction ...
Embodiment 21-37
[0036] Example 21-37 Substrate expansion of the ring-opening dichlorination reaction of cyclopropenone and oxygen heterocyclic compound
[0037] On the basis of obtaining the optimal reaction conditions (Example 20), the inventors further explored the adaptability of the optimal reaction conditions to the substrate, that is, only changing the type of reaction substrate, and preparing according to the reaction conditions of Example 20 to obtain A series of 3-chloroacrylate compounds, the results are as follows:
[0038]
[0039] b It means that the raw material consumption of cyclopropenone is 1g, and the ratio of the dosage of all the other reagents is the same as that in Example 20.
[0040]
[0041] Structural characterization of target products 1b~2b, 4b~17b:
[0042] Compound 1b:
[0043] IR: 2940, 1729, 1233, 692, 563cm -1 . 1 H NMR (500MHz, Chloroform-d) δ7.31–7.26(m,2H),7.23–7.13(m,8H),5.06–5.01(m,1H),3.99-3.93(m,1H),2.26–2.23 (m,2H),1.80–1.71(m,3H),1.53–1...
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