Multi-step reaction with 11 steps
1.1: 49 percent / iron; acetic acid / 2 h / 20 °C
2.1: 86 percent / n-Bu4NBr / tetrahydrofuran / 3.5 h / 60 °C
3.1: toluene / 21 h / Heating
4.1: aq. NaOH / ethanol / 1.5 h / Heating
5.1: iso-PrMgBr / tetrahydrofuran / 0.83 h / -25 °C
5.2: 80 percent / tetrahydrofuran / 20 °C
6.1: 87 percent / sodium borohydride / methanol / -78 - 20 °C
7.1: 96 percent / PBr3; LiBr / dimethylformamide / 0 - 20 °C
8.1: ethyl acetate / 60 °C
9.1: methanol / 1 h / Heating
10.1: aq. LiOH / tetrahydrofuran / 14 h / 20 °C
11.1: 100 percent / SOCl2 / 1 h / 20 °C
With
methanol; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; tetrabutylammomium bromide; isopropylmagnesium bromide; phosphorus tribromide; iron; acetic acid; lithium bromide;
In
tetrahydrofuran; methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmcl.2005.02.062