Multi-step reaction with 13 steps
1: 75 percent / pyridine / CH2Cl2 / 2 h / Ambient temperature
2: 94.3 percent / 2-naphthalenesulfonic acid / acetone / 8 h / Ambient temperature
3: 94 percent / triethylamine / tetrahydrofuran / Ambient temperature
4: 1.) Na / 1.) toluene, reflux, 2.) toluene, reflux, overnight
5: 70 percent / DMSO, NaCl / H2O / 15 h / 145 °C
6: 1 g / 1 M aq. KOH / methanol / Ambient temperature
7: 96 percent / diethyl ether
8: 95 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / Ambient temperature
9: 97 percent / NaBH4 / ethanol / 0.5 h / Ambient temperature
10: 88 percent / pyridine / CH2Cl2 / 15 h / -20 °C
11: 22 percent / NaN3 / dimethylformamide / 15 h / Ambient temperature
12: 86 percent / 1 M aq. KOH / methanol / 2.5 h / Ambient temperature
13: 92 percent / NaHCO3, iodine / CHCl3; H2O / 0.5 h / 0 °C
With
pyridine; potassium hydroxide; sodium tetrahydroborate; sodium azide; naphthalene-2-sulfonate; iodine; sodium; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; sodium chloride;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone;
DOI:10.1246/bcsj.65.567