Multi-step reaction with 7 steps
1: 59 percent / N-bromosuccinimide / tetrahydrofuran / 3 h / -30 °C
2: 1.) t-BuLi / 1.) pentane, ether, 23 deg C, 2 min, 2.) pentane, ether, -78 deg C, 1 h
3: 99 percent / polyphosphoric acid / 0.08 h / 0 °C
4: 100 percent / NaBH4, NiCl2*6H2O / methanol; tetrahydrofuran / 1 h / 0 °C
5: aq. Na2CO3 / methanol / 1 h / Ambient temperature
6: imidazole / dimethylformamide / 12 h / 60 °C
7: 1.) LDA, 2.) (PhCH2OCOO)2 / 1.) n-hexane, THF, -78 deg C, 2 h, 2.) n-hexane, THF, RT, 1 h
With
1H-imidazole; sodium tetrahydroborate; N-Bromosuccinimide; PPA; dibenzyl peroxydicarbonate; tert.-butyl lithium; sodium carbonate; nickel dichloride; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1248/cpb.45.1393