2,3-二氢苯并呋喃-5-甲醛合成路线 （共 30 条）
反应条件
sodium hydrogencarbonate; acetic acid in methanol; water; toluene
参考文献
Takeda Chemical Industries, Ltd.
Patent: US6348485 B1, 2002 ;
反应条件
1: ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate With N-benzyl-trimethylammonium hydroxide in tetrahydrofuran; methanol T=-78°C; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; 2: 2,3-dihydrobenzo[b]furan-5-carboxaldehyde in tetrahydrofuran; methanol T=-78°C; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Overall yield = 78 percent; diastereoselective reaction;
参考文献
Nishikawa, Keisuke; Fukuda, Hiroshi; Abe, Masato; Nakanishi, Kazunari; Taniguchi, Tomoya; Nomura, Takashi; Yamaguchi, Chihiro; Hiradate, Syuntaro; Fujii, Yoshiharu; Okuda, Katsuhiro; Shindo, Mitsuru
Phytochemistry, 2013 , vol. 96, p. 132 - 147
反应条件
Condensation; Wittig olefination;
参考文献
Coleman, Paul J.; Hutchinson, John H.; Hunt, Cecilia A.; Lu, Ping; Delaporte, Enock; Rushmore, Tom
Tetrahedron Letters, 2000 , vol. 41, # 31 p. 5803 - 5806
反应条件
1: 62 percent / pyridine; piperidine / 4 h / 100 °C 2: 90 percent / H2; AcOH / 10percent Pd/C/H20 / 1 h / 20 °C View Scheme
参考文献
Chen, Wen; Yang, Li-Juan; Li, Yan; Wang, Xue-Quan; Wang, Shao-Jie; Wan, Wei-Chao; Zhang, Hong-Bin; Yang, Xiao-Dong
Letters in Drug Design and Discovery, 2013 , vol. 10, # 7 p. 561 - 571
反应条件
1.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 1.2: 88 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 3.1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 4.1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 5.1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 6.1: SOCl2 / 75 °C 7.1: AlCl3 / 1,2-dichloro-ethane / 20 °C 8.1: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C 9.1: NaH / tetrahydrofuran / 20 °C 9.2: 60 percent / tetrahydrofuran / 20 °C View Scheme
参考文献
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori
Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239
反应条件
1.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 1.2: 88 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 3.1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C View Scheme
参考文献
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori
Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239
反应条件
hydroxylamine hydrochloride in formic acid; ethyl acetate
参考文献
Takeda Chemical Industries, Ltd.
Patent: EP1270577 A1, 2003 ;
反应条件
bromine; sodium acetate; acetic acid
T=10 - 20°C; 2 h;
参考文献
GLAXO GROUP LIMITED
Patent: WO2008/6648 A1, 2008 ;
Location in patent: Page/Page column 35 ;
反应条件
1: 62 percent / pyridine; piperidine / 4 h / 100 °C
2: 90 percent / H2; AcOH / 10percent Pd/C/H20 / 1 h / 20 °C
3: SOCl2 / 0.67 h / 75 °C
4: 4.09 g / AlCl3 / 1,2-dichloro-ethane / 0.5 h / 20 °C
View Scheme
参考文献
Chen, Wen; Yang, Li-Juan; Li, Yan; Wang, Xue-Quan; Wang, Shao-Jie; Wan, Wei-Chao; Zhang, Hong-Bin; Yang, Xiao-Dong
Letters in Drug Design and Discovery, 2013 , vol. 10, # 7 p. 561 - 571
反应条件
1: lithium alanate
2: petroleum ether; hydrogen chloride
View Scheme
参考文献
Baddeley et al.
Journal of the Chemical Society, 1956 , p. 2455,246
