Multi-step reaction with 11 steps
1.1: 85 percent / SOCl2 / hexane / 24 h / Heating
2.1: 97 percent / acetone / 0.42 h / Heating
3.1: AlCl3; CS2
4.1: 97 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C
5.1: 92 percent / pyridine / CHCl3 / 24 h / 0 - 20 °C
6.1: 90 percent / dimethylsulfoxide / 2 h / 90 °C
7.1: 86 percent / aq. NaOH / methanol / 24 h / Heating
8.1: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C
9.1: 97 percent / N,N'-dicyclohexylcarbodiimidium iodide / tetrahydrofuran / 24 h / 35 °C
10.1: nBuLi; HMPA / tetrahydrofuran; hexane / -78 °C
10.2: 76 percent / tetrahydrofuran; hexane / -78 - -50 °C
With
pyridine; carbon disulfide; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; thionyl chloride; N,N'-dicyclohexylcarbodiimidium iodide;
In
tetrahydrofuran; methanol; hexane; chloroform; dimethyl sulfoxide; acetone;
3.1: Friedel-Crafts alkylation;
DOI:10.3987/COM-03-S(P)53