Multi-step reaction with 12 steps
1: 99 percent / Pd(dba)2, Ph3P, CuI, i-Pr2NH / tetrahydrofuran / Ambient temperature
2: 97 percent / H2 / Pd/C / ethanol / 5 h / 65 °C / 3361.5 Torr
3: 99 percent / 1 M NaOH / tetrahydrofuran / Heating
4: AlCl3 / CS2; chlorobenzene / Heating
5: 3 M KOH
6: 1.) t-BuONO, BF3-Et2O, 2.) K2CO3 / 1.) CH2Cl2, 0 deg C, 30 min, 2.) 2 h
8: 94 percent / MeI / 120 °C
9: 85 percent / Pd(dba)2, Ph3P, CuI, i-Pr2NH / tetrahydrofuran / 72 h
10: 95 percent / MeI / 120 °C
11: 87 percent / Pd(dba)2, Ph3P, CuI, i-Pr2NH / tetrahydrofuran / 48 h
12: 92 percent / MeI / 120 °C
With
potassium hydroxide; sodium hydroxide; copper(l) iodide; aluminium trichloride; tert.-butylnitrite; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; diisopropylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0); methyl iodide;
palladium on activated charcoal;
In
tetrahydrofuran; carbon disulfide; ethanol; chlorobenzene;
DOI:10.1021/jo962336q