1.1: 73 percent / methanol / 24 h / Heating 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h 2.2: 86 percent / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 93 percent / lithium naphthalenide / tetrahydrofuran / 0.33 h / -78 °C 4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C 4.2: 99 percent / tetrahydrofuran; toluene / 0.33 h / -23 °C 5.1: tributylamine; bis(acetato)bis(triphenylphosphine)palladium(II); formic acid / dimethylformamide / 7 h / 60 °C 6.1: 14 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

sodium tetrahydroborate; diethyl methoxy borane

hydrogenchloride 1.)dioxane; 100 deg C; 30 min 2.) THF; R.T; 17 h; Multistep reaction;