Multi-step reaction with 7 steps
1: 96 percent / p-toluenesulfonic acid / various solvent(s) / 3 h
2: 58 percent / pyridine / 1) 4 h, -20 deg C, 2) 12 h, -15 deg C
3: 84 percent / 80percent sodium hydride in paraffin oil / tetrahydrofuran / 1) 1 h, 0 deg C, 2) 4 h, 20 deg C
4: 94 percent / sodium iodide, sodium acetate, aq. acetic acid, zinc dust / 2 h / 0 °C
5: 87 percent / H2 / 5percent Pt on carbon / methyl acetate / 10 h
6: 1.) n-BuLi, N,N-diisopropylamine / 1.) THF, hexane, 0 deg C, then -78 deg C, 30 min, 2.) -78 deg C, 30 min
7: 2M KOH / methanol; H2O / 4 h / Heating
With
potassium hydroxide; n-butyllithium; hydrogen; sodium acetate; sodium hydride; toluene-4-sulfonic acid; acetic acid; diisopropylamine; sodium iodide; zinc;
platinum on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; acetic acid methyl ester; water;