3,4-二甲氧基苯乙酸合成路线 （共 159 条）
反应条件
1: SOCl2 / diethyl ether / 0.5 h / Heating
2: 69 percent / sodium acetate / diethyl ether; tetrahydrofuran / Ambient temperature
3: 94 percent / NaBH4 / methanol / 0 - 5 °C
4: 41 percent / PPA, 85 percent H3PO4 / 1 h / 100 °C
5: 52 percent / DDQ / benzene / 17 h / Heating
View Scheme
参考文献
Berney, Daniel; Schuh, Karlheinz
Helvetica Chimica Acta, 1981 , vol. 64, # 2 p. 373 - 378
反应条件
1: SOCl2 / diethyl ether / 0.5 h / Heating
2: 69 percent / sodium acetate / diethyl ether; tetrahydrofuran / Ambient temperature
3: 94 percent / NaBH4 / methanol / 0 - 5 °C
4: 41 percent / PPA, 85 percent H3PO4 / 1 h / 100 °C
5: 52 percent / DDQ / benzene / 17 h / Heating
6: 58 percent / CH2Cl2 / Ambient temperature
View Scheme
参考文献
Berney, Daniel; Schuh, Karlheinz
Helvetica Chimica Acta, 1981 , vol. 64, # 2 p. 373 - 378
反应条件
1.1: 1,2-dichloro-ethane; benzotriazol-1-ol / dichloromethane / 0.5 h / 0 °C
1.2: 20 °C
2.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C
3.1: potassium tert-butylate / tert-butyl alcohol / 0 - 20 °C / |Inert atmosphere
View Scheme
参考文献
Bin, Jin Wen; Wong, Iris L. K.; Hu, Xuesen; Yu, Zhang Xiao; Xing, Li Fu; Jiang, Tao; Chow, Larry M. C.; Biao, Wan Sheng
Journal of Medicinal Chemistry, 2013 , vol. 56, # 22 p. 9057 - 9070
反应条件
1.1: sulfuric acid / 0.5 h / |Reflux
2.1: sodium tetrahydroborate; calcium chloride / ethanol / 16 h / 0 - 20 °C
3.1: toluene-4-sulfonic acid / toluene / 18 h / |Dean-Stark; |Reflux
4.1: palladium diacetate; PCy3∙HBF4; potassium carbonate / dimethyl sulfoxide / 0.17 h / 140 °C / 10343.2 Torr / |Microwave irradiation
5.1: hydrogen bromide / 0.5 h / 10 °C
5.2: 2 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
7.1: sodium tris(acetoxy)borohydride / tetrahydrofuran; dichloromethane / 2 h / 0 - 20 °C
View Scheme
参考文献
Kapadia, Nirav; Harding, Wayne
Tetrahedron, 2013 , vol. 69, # 42 p. 8914 - 8920
反应条件
T=200°C; 0.416667 h;
参考文献
Shcherbakova, I. V.; Kuznetsov, E. V.
Journal of Organic Chemistry USSR (English Translation), 1989 , p. 149 - 154
Zhurnal Organicheskoi Khimii, 1989 , vol. 25, # 1 p. 164 - 171
反应条件
dicyclohexyl-carbodiimide in ethyl acetate
3 h;
参考文献
King, Frank D.
Tetrahedron, 2007 , vol. 63, # 9 p. 2053 - 2056
反应条件
hydrogenchloride; N-chloro-succinimide in tetrahydrofuran; water
T=-10 - 100°C; 2 h; Product distribution / selectivity;
参考文献
MALLINCKRODT INC.
Patent: WO2006/52430 A2, 2006 ;
Location in patent: Page/Page column 24-26 ;
反应条件
1.1: sulfuric acid / Reflux
2.1: tin(ll) chloride / 20 °C
3.1: hydrazine hydrate / ethanol / 3 h / 150 °C
3.2: 0.5 h / Reflux
4.1: N,N-dimethyl-aniline; trichlorophosphate / chloroform / 120 °C
5.1: tetrahydrofuran / -78 °C
View Scheme
参考文献
Bihel, Frederic J.J.; Justiniano, Helene; Schmitt, Martine; Hellal, Malik; Ibrahim, Mohamed A.; Lugnier, Claire; Bourguignon, Jean-Jacques
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 21 p. 6567 - 6572
反应条件
1: 81 percent / thionyl chloride / CH2Cl2 / 1 h / Heating
2: triethylamine / CH2Cl2 / 1 h / Ambient temperature
3: 75 percent / glacial acetic acid, conc. HCl / 17 h / Ambient temperature
4: 1.) potassium tert-butoxide / 1.) DMSO, RT, 30 min, 2.) RT, 30 min
5: 2 h / 90 - 95 °C
6: H2 / Pd/C / acetic acid / 10 h / 3750.3 Torr / Ambient temperature
View Scheme
参考文献
Reiffen; Eberlein; Muller; Psiorz; Noll; Heider; Lillie; Kobinger; Luger
Journal of Medicinal Chemistry, 1990 , vol. 33, # 5 p. 1496 - 1504
反应条件
1: HClO4
2: LDA
3: t-BuONa
4: CF3CO2H
5: NaOH
6: diisobutylaluminium hydride (DIBAL) / hexane
7: PBr3
9: NH2NH2
View Scheme
参考文献
Bey; Fozard; Lacoste; McDonald; Zreika; Palfreyman
Journal of Medicinal Chemistry, 1984 , vol. 27, # 1 p. 9 - 10
