6-甲氧基-N,N-二乙基苯酰胺-2-甲醛合成路线 （共 8 条）
反应条件
1: 2-methoxy-N,N-diethyl-benzamide With tert.-butyl lithium in tetrahydrofuran; pentane
T=-78°C; 1.5 h; Inert atmosphere;
2: N,N-dimethyl-formamide in tetrahydrofuran; pentane
T=-78°C; 3 h;
参考文献
Naysmith, Briar J.; Brimble, Margaret A.
Organic Letters, 2013 , vol. 15, # 8 p. 2006 - 2009
反应条件
1: With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in tetrahydrofuran; cyclohexane
T=-78°C; 0.5 h;
2: 2-methoxy-N,N-diethyl-benzamide in tetrahydrofuran; cyclohexane
T=-78°C; 2.83333 h;
3: N,N-dimethyl-formamide in tetrahydrofuran; cyclohexane
0.5 h;
参考文献
NOVARTIS AG; NOVARTIS PHARMA GMBH
Patent: WO2007/6533 A2, 2007 ;
Location in patent: Page/Page column 51 ;
反应条件
1.1: SOCl2 / toluene / 2 h / Heating
2.1: diethyl ether / 1 h
3.1: t-BuLi; TMEDA / tetrahydrofuran / 1.5 h / -78 °C
3.2: 70 percent / tetrahydrofuran
View Scheme
参考文献
Gibson, Jennifer S.; Andrey, Olivier; Brimble, Margaret A.
Synthesis, 2007 , # 17 p. 2611 - 2613
反应条件
1.1: diethyl ether / 1 h
2.1: t-BuLi; TMEDA / tetrahydrofuran / 1.5 h / -78 °C
2.2: 70 percent / tetrahydrofuran
View Scheme
参考文献
Gibson, Jennifer S.; Andrey, Olivier; Brimble, Margaret A.
Synthesis, 2007 , # 17 p. 2611 - 2613
反应条件
hydrogenchloride; acetic acid
T=120°C; 18 h;
参考文献
Vamshikrishna; Srihari
Tetrahedron Asymmetry, 2012 , vol. 23, # 22-23 p. 1584 - 1587
反应条件
hydrogenchloride; water; acetic acid
12 h; Reflux; Overall yield = 98 percent;
参考文献
Mamidyala, Sreeman K.; Cooper, Matthew A.
Chemical Communications, 2013 , vol. 49, # 75 p. 8407 - 8409
反应条件
1: 1) LDA / 1) a) THF, 0 deg C, 1.5 h, b) 40-45 deg C, 0.5 h, 2) THF, 40 deg C, 12 h
2: p-toluenesulfonic acid / toluene / 12 h / Heating
3: 54 percent / BBr3 / CH2Cl2 / a) -78 deg C, 1 h, b) without cooling, 20 h
View Scheme
参考文献
De Silva; Reed; Billedeau; Wang; Norris; Snieckus
Tetrahedron, 1992 , vol. 48, # 23 p. 4863 - 4878
反应条件
hydrogenchloride; water; acetic acid
12 h; Reflux; Overall yield = 98 percent;
参考文献
Mamidyala, Sreeman K.; Cooper, Matthew A.
Chemical Communications, 2013 , vol. 49, # 75 p. 8407 - 8409
