4-(4-羟基丁基)苯甲酸甲酯合成路线 （共 13 条）
反应条件
sodium acetate; pyridinium chlorochromate in dichloromethane T=20°C; 3 h;
参考文献
Taylor, Edward C.; Liu, Bin
Journal of Organic Chemistry, 2003 , vol. 68, # 26 p. 9938 - 9947
反应条件
sodium acetate; pyridinium chlorochromate in dichloromethane
参考文献
The Trustees of Princeton University
Patent: US6066732 A1, 2000 ;
反应条件
1: pyridine / tetrahydrofuran / 20 °C 2: sodium azide / dimethylformamide / 20 °C 3: 53 percent / Ph3P; H2O / tetrahydrofuran / 20 °C View Scheme
参考文献
Hirsh, Andrew J.; Molino, Bruce F.; Zhang, Jianzhong; Astakhova, Nadezhda; Geiss, William B.; Sargent, Bruce J.; Swenson, Brian D.; Usyatinsky, Alexander; Wyle, Michael J.; Boucher, Richard C.; Smith, Rick T.; Zamurs, Andra; Johnson, M. Ross
Journal of Medicinal Chemistry, 2006 , vol. 49, # 14 p. 4098 - 4115
反应条件
1: pyridine / tetrahydrofuran / 20 °C 2: sodium azide / dimethylformamide / 20 °C View Scheme
参考文献
Hirsh, Andrew J.; Molino, Bruce F.; Zhang, Jianzhong; Astakhova, Nadezhda; Geiss, William B.; Sargent, Bruce J.; Swenson, Brian D.; Usyatinsky, Alexander; Wyle, Michael J.; Boucher, Richard C.; Smith, Rick T.; Zamurs, Andra; Johnson, M. Ross
Journal of Medicinal Chemistry, 2006 , vol. 49, # 14 p. 4098 - 4115
反应条件
1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / -10 - 20 °C / pH 9.5 / |Large scale 2: DBBA; hydrogen bromide; acetic acid / dichloromethane / 25 °C / |Large scale 3: sodium acetate / water; acetonitrile / 3 h / 40 °C / |Large scale 4: sodium hydroxide / water / 1.5 h / 40 °C / |Large scale 5: 2-chloro-4,6-dimethoxy-[1,3,5]triazine; 4-methylmorpholine N-oxide / N,N-dimethyl-formamide / 1.5 h / 25 °C / |Large scale View Scheme
参考文献
Barnett, Charles J.; Wilson, Thomas M.; Kobierski, Michael E.
Organic Process Research and Development, 1999 , vol. 3, # 3 p. 184 - 188
反应条件
1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / -10 - 20 °C / pH 9.5 / |Large scale 2: DBBA; hydrogen bromide; acetic acid / dichloromethane / 25 °C / |Large scale 3: sodium acetate / water; acetonitrile / 3 h / 40 °C / |Large scale 4: sodium hydroxide / water / 1.5 h / 40 °C / |Large scale View Scheme
参考文献
Barnett, Charles J.; Wilson, Thomas M.; Kobierski, Michael E.
Organic Process Research and Development, 1999 , vol. 3, # 3 p. 184 - 188
反应条件
1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / -10 - 20 °C / pH 9.5 / |Large scale 2: DBBA; hydrogen bromide; acetic acid / dichloromethane / 25 °C / |Large scale 3: sodium acetate / water; acetonitrile / 3 h / 40 °C / |Large scale 4: sodium hydroxide / water / 1.5 h / 40 °C / |Large scale 5: 2-chloro-4,6-dimethoxy-[1,3,5]triazine; 4-methylmorpholine N-oxide / N,N-dimethyl-formamide / 1.5 h / 25 °C / |Large scale 6: ethanol / 3 h / |Reflux; |Large scale View Scheme
参考文献
Barnett, Charles J.; Wilson, Thomas M.; Kobierski, Michael E.
Organic Process Research and Development, 1999 , vol. 3, # 3 p. 184 - 188
反应条件
triethylamine in diethyl ether T=0 - 20°C; 4 h; Yield given;
参考文献
Hirsh, Andrew J.; Molino, Bruce F.; Zhang, Jianzhong; Astakhova, Nadezhda; Geiss, William B.; Sargent, Bruce J.; Swenson, Brian D.; Usyatinsky, Alexander; Wyle, Michael J.; Boucher, Richard C.; Smith, Rick T.; Zamurs, Andra; Johnson, M. Ross
Journal of Medicinal Chemistry, 2006 , vol. 49, # 14 p. 4098 - 4115
反应条件
1: 63 percent / aq. CrO3; sulfuric acid / acetone / 0 - 20 °C
2: oxalyl chloride / CH2Cl2 / 1 h / Heating
3: diethyl ether / 1.17 h / cooling
4: 2 g / aq. HCl / diethyl ether / 1.5 h / Heating
View Scheme
参考文献
Gangjee, Aleem; Zeng, Yibin; McGuire, John J.; Mehraein, Farideh; Kisliuk, Roy L.
Journal of Medicinal Chemistry, 2004 , vol. 47, # 27 p. 6893 - 6901
反应条件
1: triethylamine / diethyl ether / 4 h / 0 - 20 °C
2: 1.) NaH / 1.) THF, 0 deg C -> room temperature, 2.) room temperature, 12 h; reflux, 6 h
3: 1.) sodium methoxide / 1.) anhydrous methanol, nitrogen atmosphere, 0.5 h, 2.) anhydrous dimethylformamide, mild warming, 12 h
4: 2.33 g / 1N sodium hydroxide / 18 h / Ambient temperature
View Scheme
参考文献
Taylor, Edward C.; Harrington, Philip M.; Shih, Chuan
Heterocycles, 1989 , vol. 28, # 2 p. 1169 - 1178
