Multi-step reaction with 13 steps
1: 87 percent / LiAlH4 / diethyl ether / 0.5 h / -78 °C
2: 94 percent / pyridine; tetrahydrofuran / 0.5 h / 20 °C
3: ethanol; hexane / recrystallization
4: 87 percent / 40 percent KOH / H2O; methanol / 3.5 h / 60 °C
5: 97 percent / imidazole / dimethylformamide / 1.5 h
6: 5.0 M Me2AlCl / hexane; CH2Cl2 / 1.5 h / -40 °C
7: 96 percent / DMAP / pyridine / 2.5 h / 40 °C
8: 83 percent / I2 / acetic acid / 1 h
9: 96 percent / (n-Bu)3SnH / benzene / 0.17 h / 60 °C
10: 94 percent / dimethylsulfoxide / 1 h
11: 93 percent / m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -20 - 0 °C
12: 1.) K2CO3; 2.) DMAP, (i-Pr)2NEt / 1.) MeOH, 2 h; 2.) DMF, 60 deg C, 5 h
With
1H-imidazole; dmap; potassium hydroxide; lithium aluminium tetrahydride; iodine; tri-n-butyl-tin hydride; dimethylaluminum chloride; potassium carbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;