4-甲氧基-2-苯并呋喃-1(3H)-酮合成路线 （共 48 条）
反应条件
1.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
2.1: potassium carbonate / acetone / 18 h / Reflux
3.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / 1 h / -78 °C / Inert atmosphere
3.2: 0.83 h / -78 - 20 °C / Inert atmosphere
3.3: 0 °C / pH 5 - 6 / Inert atmosphere
4.1: sodium tetrahydroborate / methanol / 0.75 h / 0 - 20 °C / Inert atmosphere
5.1: hydrogenchloride / methanol; water / 16 h / 0 °C / pH 4 - 5 / Inert atmosphere; Reflux
View Scheme
参考文献
Egan, Ben A.; Paradowski, Michael; Thomas, Lynne H.; Marquez, Rodolfo
Organic Letters, 2011 , vol. 13, # 8 p. 2086 - 2089
反应条件
1.1: potassium carbonate / acetone / 18 h / Reflux
2.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / 1 h / -78 °C / Inert atmosphere
2.2: 0.83 h / -78 - 20 °C / Inert atmosphere
2.3: 0 °C / pH 5 - 6 / Inert atmosphere
3.1: sodium tetrahydroborate / methanol / 0.75 h / 0 - 20 °C / Inert atmosphere
4.1: hydrogenchloride / methanol; water / 16 h / 0 °C / pH 4 - 5 / Inert atmosphere; Reflux
View Scheme
参考文献
Egan, Ben A.; Paradowski, Michael; Thomas, Lynne H.; Marquez, Rodolfo
Organic Letters, 2011 , vol. 13, # 8 p. 2086 - 2089
反应条件
1: aqueous hydrochloric acid; sulfuric acid / 50 °C / Einleiten von Chlorwasserstoff
2: Raney nickel; ethanol / 150 - 200 °C / 25742.8 Torr / Hydrogenation
3: aq. NaOH solution
View Scheme
参考文献
Buehler; Powers; Michels
Journal of the American Chemical Society, 1944 , vol. 66, p. 417
反应条件
2: sodium borohydride
View Scheme
参考文献
Dang, Qun; Brown, Brian S.; Van Poelje, Paul D.; Colby, Timothy J.; Erion, Mark D.
Bioorganic and Medicinal Chemistry Letters, 1999 , vol. 9, # 11 p. 1505 - 1510
反应条件
1: hydrolysis
2: acetic anhydride / Heating
3: L-Selectride / tetrahydrofuran / 2 h / Ambient temperature
View Scheme
参考文献
Makhlouf, Mansour A.; Rickborn, Bruce
Journal of Organic Chemistry, 1981 , vol. 46, # 23 p. 4810 - 4811
反应条件
hydrogenchloride; lithium hydroxide; copper; zinc
1.) water, boiling, 1 h, 2.) pH 1; Yield given. Multistep reaction;
参考文献
Epsztajn, Jan; Jozwiak, Andrzej; Szczesniak, Aleksandra K.
Tetrahedron, 1993 , vol. 49, # 4 p. 929 - 938
反应条件
1.1: oxalyl chloride / CH2Cl2; dimethylformamide / 1.5 h
2.1: 198 mg / Et3N / CH2Cl2 / 2 h
3.1: O3 / CH2Cl2 / -78 °C
3.2: 100 percent / Ph3P / CH2Cl2 / -78 - 20 °C
4.1: SmI2 / tetrahydrofuran / 0.5 h / -78 °C
View Scheme
参考文献
Laursen, Bolette; Denieul, Marie-Pierre; Skrydstrup, Troels
Tetrahedron, 2002 , vol. 58, # 11 p. 2231 - 2238
反应条件
1.1: O3 / CH2Cl2 / -78 °C
1.2: 100 percent / Ph3P / CH2Cl2 / -78 - 20 °C
2.1: SmI2 / tetrahydrofuran / 0.5 h / -78 °C
View Scheme
参考文献
Laursen, Bolette; Denieul, Marie-Pierre; Skrydstrup, Troels
Tetrahedron, 2002 , vol. 58, # 11 p. 2231 - 2238
反应条件
1: 75 percent / BuLi / tetrahydrofuran / 1.) -78 deg C, 0.5 h; 0 deg C, 0.1 h, 2.) -78 deg C, 1 h; r.t., 1 h
2: Zn-Cu, LiOH / H2O / 1 h / Heating
3: HCl / H2O
View Scheme
参考文献
Epsztajn, Jan; Jozwiak, Andrzej; Szczesniak, Aleksandra K.
Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 16 p. 2563 - 2567
反应条件
1: 92 percent / N-bromosuccinimide (NBS) / CCl4 / 2.5 h / Heating; Irradiation
2: sodium acetate, glacial acetic acid / 3 h / Heating
3: 91 percent / potassium carbonate / methanol; H2O / 4 h / Ambient temperature
4: 85 percent / Jones reagent / acetone / Heating
View Scheme
参考文献
Box, Vernon, G. S.; Yiannikouros, George P.
Heterocycles, 1990 , vol. 31, # 7 p. 1261 - 1270
