Multi-step reaction with 13 steps
1: 42 percent / Zn / benzene / 1 h / Heating
2: 92 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / diethyl ether / 0.5 h / Ambient temperature
3: 14 percent / Zn(BH4)2 / diethyl ether / 0 °C
4: 96 percent / LiBH4 / tetrahydrofuran / 0.5 h / Ambient temperature
6: 99 percent / imidazole / dimethylformamide / 1 h / 0 °C
7: 98 percent / KH / tetrahydrofuran / 3 h / Ambient temperature
8: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature
9: 1.) Ph3P, CBr4 / 1.) THF, 0 deg C - RT, 50 min, 2.) THF, DMSO, 60 deg C, 1 h
10: aq. NaOH / ethanol / 3 h / Heating
11: diethyl ether
12: 1.) LDA, 3.) aq. NaOH
13: methanol; diethyl ether / 0.5 h
With
1H-imidazole; sodium hydroxide; lithium borohydride; zinc(II) tetrahydroborate; carbon tetrabromide; tetrabutyl ammonium fluoride; potassium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; N,N-dimethyl-formamide; benzene;
DOI:10.1248/cpb.43.1111