Multi-step reaction with 8 steps
1: 1.) KOtBu / 1.) THF, 0 deg C, 1h, 2.) THF, -78 deg C, 1 h; 0 deg C, 1 h.
2: 1.) NiCl2, NaBH4, 2.) LiAlH4 / 1.) MeOH, room temperature, 2 h, 2.) THF, -78 deg C, 3.5 h; room temperature, 30 min.
3: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 10 min, 2.) -78 deg C, 10 min; 0 deg C, 15 min.
4: 1.) dibutylboron triflate, Et3N / 1.) CH2Cl2, 0 deg C, 30 min, 2.) CH2Cl2, -78 deg C, 1.5 h; 0 deg C, 15 min.
5: 77 percent / Ph3P, diethyl azodicarboxylate / benzene / 33 h / Ambient temperature
7: 94 percent / H2 / Pd(OH)2 / dioxane / 1.8 h / 40 °C
8: 58 percent / Ph3P, diethyl azodicarboxylate / benzene / 2.5 h / Ambient temperature
With
sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; nickel dichloride; diethylazodicarboxylate;
palladium dihydroxide;
In
1,4-dioxane; benzene;
DOI:10.1021/jo9608228