3-羟基-3-甲基-2-丁酮合成路线 （共 82 条）
反应条件
1: 89.1 percent / EtONa / ethanol / 22 h / 0 °C
2: 88.3 percent / p-TsOH*H2O / benzene / 10 h / Heating
3: 1.) O3, 2.) Me2S / 1.) MeOH, -78 deg C, 10 min, 2.) a) -78 deg C, 20 min, b) 26 deg C, 2 h
View Scheme
参考文献
Semple, J. Edward; Guthrie, Anne E.; Joullie, Madeleine M.
Tetrahedron Letters, 1980 , vol. 21, # 47 p. 4561 - 4564
反应条件
1: 15 percent / LiNPr2 / tetrahydrofuran
2: MsCl / pyridine
3: 96.1 percent / acetic acid; tetrahydrofuran; H2O / 2 h / 50 °C
4: 90 percent / pyridine / Ambient temperature
5: 80.4 percent / Me3SiOTf / CH2Cl2 / 7 h / 0 - 5 °C
6: 93.1 percent / K2CO3 / methanol; H2O / Ambient temperature
7: 1.) n-BuLi, p-TsCl, HMPA; 2.) LiBr / 1.) n-hexane, ether, 0 deg C, 5 min; 2.) n-hexane, ether, RT, overnight
9: 63.2 percent / CaCO3, NCS / dimethylformamide; H2O / 0 - 25 °C
10: 50 percent / DBU / tetrahydrofuran / 4 h / Heating
11: 1.) EtMgBr / 1.) ether, RT, 30 min; 2.) 100 deg C, 10 min
12: 31.5 percent / AcOH / H2O / 0.5 h / Heating
View Scheme
参考文献
Mori, Kenji; Fujioka, Takafumi
Tetrahedron, 1984 , vol. 40, # 14 p. 2711 - 2720
参考文献
Sampson, Paul; Roussis, Vassilios; Drtina, Gary J.; Koerwitz, Frederick L.; Wiemer, David F.
Journal of Organic Chemistry, 1986 , vol. 51, # 13 p. 2525 - 2529
反应条件
triethylamine; phosphorus trichoride in diethyl ether
T=18 - 25°C; 2 h;
参考文献
Mukhametov, F. S.; Eliseenkova, R. M.; Korshin, E. E.
J. Gen. Chem. USSR (Engl. Transl.), 1991 , vol. 61, # 11 p. 2539 - 2547,2356 - 2362
反应条件
n-butyllithium; diisopropylamine
1.) THF, hexane, 2.) THF, hexane, -15 deg C, 3,) THF, hexane, 25 deg C; Yield given. Multistep reaction;
参考文献
Limat, Dominique; Schlosser, Manfred
Tetrahedron, 1995 , vol. 51, # 20 p. 5799 - 5806
反应条件
1.1: 95 percent / Br2 / methanol / 24 h / 23 °C
2.1: KOAc / 4 h / 95 °C
2.2: 28 percent / 24 h / 23 °C
View Scheme
参考文献
Gauthier Jr., Donald R.; Limanto, John; Devine, Paul N.; Desmond, Richard A.; Szumigala Jr., Ronald H.; Foster, Bruce S.; Volante
Journal of Organic Chemistry, 2005 , vol. 70, # 15 p. 5938 - 5945
反应条件
1.1: DMAP; Et3N / CH2Cl2 / 16 h / 20 °C
2.1: boron trifluoride etherate / CH2Cl2 / 1.5 h / -65 - 0 °C
2.2: diisopropylethylamine / CH2Cl2 / 7.95 h / -65 - 20 °C
3.1: NaOMe; EtOH / 1 h / 24 - 60 °C
3.2: 74 percent / ethanol / 4 h / 45 - 60 °C
View Scheme
参考文献
Jensen, Mark S.; Hoerrner, R. Scott; Li, Wenjie; Nelson, Dorian P.; Javadi, Gary J.; Dormer, Peter G.; Cai, Dongwei; Larsen, Robert D.
Journal of Organic Chemistry, 2005 , vol. 70, # 15 p. 6034 - 6039
反应条件
1: 66 percent / LiOH*H2O / methanol; H2O / 20 °C
2: 93 percent / O2; CuCl; Na2HPO4 / PdCl2 / 1,2-dimethoxy-ethane / 144 h / 48 - 80 °C
View Scheme
参考文献
Smith, Amos B.; Levenberg, Patricia A.; Jerris, Paula J.; Scarborough, Robert M.; Wovkulich, Peter M.
Journal of the American Chemical Society, 1981 , vol. 103, # 6 p. 1501 - 1513
参考文献
Bergmann et al.
Recueil des Travaux Chimiques des Pays-Bas, 1952 , vol. 71, p. 168,192
Journal of the American Chemical Society, 1953 , vol. 75, p. 358
反应条件
1: 485 °C / Pyrolysis.Reaktion des Essigsaeureesters
View Scheme
参考文献
McMahon et al.
Journal of the American Chemical Society, 1948 , vol. 70, p. 2976
