Multi-step reaction with 11 steps
1: 98.6 percent / diethyl ether / 1.) -78 deg C, 1.5 h, 2.) from -78 deg C to -30 deg C, 2 h
2: 100 percent / N,N-diethylaniline / CH2Cl2 / 22 h / 22 °C
3: Na, ethanol / diethyl ether; liquid ammonia / 1 h / -78 °C
4: 100 percent / pyridine / 120 h / 0 °C
5: 100 percent / p-toluenesulfonic acid / methanol / 4 h / 22 °C
6: 92 percent / H2 / 5percent Pd/C / ethanol; ethyl acetate / 9 h / 22 °C
7: 58 percent / dimethylformamide / 0.6 h / 84 °C
8: 4.6percent methanolic HCl / 4 h / 55 °C
9: 74 percent / BF3*OEt2 / CHCl3 / 2 h / 22 °C
10: 100 percent / triethylamine / CH2Cl2 / 0.5 h / 0 °C
11: 60 percent / LiBr / 1,2-dimethoxy-ethane / 0.5 h / 62 °C
With
pyridine; hydrogenchloride; ethanol; boron trifluoride diethyl etherate; hydrogen; sodium; toluene-4-sulfonic acid; triethylamine; N,N-diethylaniline; lithium bromide;
palladium on activated charcoal;
In
methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; chloroform; ammonia; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo00381a027