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Scalable Microwave-Assisted Johnson–Claisen Rearrangement with a Continuous Flow Microwave System
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2018-07-23 00:00:00 , DOI: 10.1021/acs.oprd.8b00185 Hiromichi Egami 1 , Souma Tamaoki 1 , Masato Abe 2 , Noriyuki Ohneda 3 , Takeo Yoshimura 3 , Tadashi Okamoto 3 , Hiromichi Odajima 3 , Nobuyuki Mase 2 , Kazuhiro Takeda 2 , Yoshitaka Hamashima 1
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2018-07-23 00:00:00 , DOI: 10.1021/acs.oprd.8b00185 Hiromichi Egami 1 , Souma Tamaoki 1 , Masato Abe 2 , Noriyuki Ohneda 3 , Takeo Yoshimura 3 , Tadashi Okamoto 3 , Hiromichi Odajima 3 , Nobuyuki Mase 2 , Kazuhiro Takeda 2 , Yoshitaka Hamashima 1
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We demonstrated the rapid Johnson–Claisen rearrangement of allyl alcohol and triethyl orthoacetate with a continuous flow apparatus combined with a microwave reactor. The reaction could be carried out without solvent, and only a catalytic amount of acetic acid was sufficient to promote the reaction under microwave irradiation conditions. To confirm the optimal reaction conditions found experimentally, we performed Design of Experiments (DoE) by the Nelder–Mead method and a least-squares method regarding the amount of acetic acid and the flow rate. Consequently, the highest yield of the desired γ,δ-unsaturated ester was obtained, and the productivity at the reaction step of the continuous process was 89.5 g/h under the optimal conditions, suggesting that 2.1 kg of the product would be theoretically obtained in 1 day. We also investigated the Johnson–Claisen rearrangement using other allylic alcohols, and the corresponding products were obtained in good to high yields per unit of time.
中文翻译：
连续流微波系统可扩展的微波辅助约翰逊·克莱森重排
我们用连续流动装置结合微波反应器证明了烯丙醇和原乙酸三乙酯的约翰逊-克莱森快速重排。该反应可以在没有溶剂的情况下进行，并且仅催化量的乙酸足以在微波辐射条件下促进反应。为了确认实验中发现的最佳反应条件，我们通过Nelder–Mead方法和最小二乘法对乙酸的量和流速进行了实验设计（DoE）。因此，获得了所需的γ，δ-不饱和酯的最高收率，并且在最佳条件下，连续过程的反应步骤的生产率为89.5g / h，这表明理论上可以在室温下获得2.1kg的产物。 1天。
更新日期：2018-07-23
中文翻译：
连续流微波系统可扩展的微波辅助约翰逊·克莱森重排
我们用连续流动装置结合微波反应器证明了烯丙醇和原乙酸三乙酯的约翰逊-克莱森快速重排。该反应可以在没有溶剂的情况下进行，并且仅催化量的乙酸足以在微波辐射条件下促进反应。为了确认实验中发现的最佳反应条件，我们通过Nelder–Mead方法和最小二乘法对乙酸的量和流速进行了实验设计（DoE）。因此，获得了所需的γ，δ-不饱和酯的最高收率，并且在最佳条件下，连续过程的反应步骤的生产率为89.5g / h，这表明理论上可以在室温下获得2.1kg的产物。 1天。
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