Multi-step reaction with 15 steps
1: 85.9 percent / imidazole / dimethylformamide / 3 h
2: 72.9 percent / aq. LiOH / methanol / 81 h
3: oxalyl chloride, DMF / benzene / 0.42 h
4: 1.) n-BuLi / 1.) benzene, hexane, 30 min, 2.) benzene, hexane, 80 deg C, 30 min
5: CH2Cl2 / 1.33 h / -30 - 0 °C
6: 71.4 percent / LiBF4, p-toluenesulfonic acid / acetone; CH2Cl2 / 12 h
7: LiAlH4 / tetrahydrofuran / 4 h / -78 - 25 °C
8: 56.2 percent / p-toluenesulfonic acid / benzene / 22 h
9: 73.8 percent / BaO, Ba(OH)2 / dimethylformamide / 1.) RT, 0.5 h, 2.) 40 deg C, 34 h
10: 74.5 percent / N',N'-dimethylaminopyridine / CH2Cl2 / 28 h
11: 10percent aq. HCl / tetrahydrofuran / 26 h / 50 °C
12: p-toluenesulfonic acid / acetone; tetrahydrofuran / 6 h
13: 90.4 percent / H2, acetic acid / 10percent Pd/C / ethyl acetate / 7 h
14: 91.4 percent / N',N'-dimethylaminopyridine / CH2Cl2 / 2.25 h
15: 96.7 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.33 h / -78 °C
With
1H-imidazole; hydrogenchloride; barium dihydroxide; lithium hydroxide; lithium aluminium tetrahydride; lithium tetrafluoroborate; n-butyllithium; oxalyl dichloride; N',N'-dimethylaminopyridine; hydrogen; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; barium(II) oxide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo00385a024
