1: 86 percent 2: 92 percent 3: 86 percent / PhSeO2K, 18-crown-6 / acetonitrile 4: NaH / tetrahydrofuran 5: H2 / Pd-C 6: pyH(1+)*Br3(1-) 7: OH(1-) 8: 1.) LiOH, n-BuLi / tetrahydrofuran / -78 deg C, 2 h than -40 deg C, 3 h View Scheme

1.1: sec-BuLi; TMEDA / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C 1.2: 79 percent / tetrahydrofuran; cyclohexane / -78 - 20 °C 2.1: 90 percent / CsF / dimethylformamide; H2O / Heating 3.1: 69 percent / LDA / tetrahydrofuran / -78 - 20 °C 4.1: 77 percent / NaBH4; NaOH / methanol; H2O / 13 h / Heating View Scheme

1: 86 percent 2: 92 percent 3: 86 percent / PhSeO2K, 18-crown-6 / acetonitrile View Scheme

1: N,N-(diethyl)-3-methoxybenzene-1-carboxamide With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in tetrahydrofuran; hexane T=-78°C; 1 h; 2: chloro-trimethyl-silane in tetrahydrofuran; hexane T=-78 - 22°C; 18 h; Further stages.;

1.1: 89 percent / thionyl chloride 2.1: sec-butyllithium; TMEDA / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: 90 percent / hexane; tetrahydrofuran / 18 h / -78 - 22 °C View Scheme

1.1: sec-BuLi; TMEDA / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C 1.2: 79 percent / tetrahydrofuran; cyclohexane / -78 - 20 °C 2.1: 90 percent / CsF / dimethylformamide; H2O / Heating View Scheme

1.1: TMEDA; s-BuLi / diethyl ether; hexane / 2 h / 0 °C 1.2: B(OMe)3 / diethyl ether; hexane / 2 h / 25 °C 2.1: 1.28 g / Pd(PPh3)4; aq. K2CO3 / 1,2-dimethoxy-ethane / 19 h / Heating 3.1: 92 percent / TBAF / tetrahydrofuran / 16 h / 25 °C 4.1: 93 percent / diisopropylazodicarboxylate; Ph3P / CH2Cl2 / 4 h / 25 °C 5.1: n-BuLi / hexane; diethyl ether / 0.08 h / -78 °C 5.2: (i-PrO)3B / diethyl ether; hexane / 0.5 h / -78 - 25 °C 5.3: 88 percent / aq. H2O2 / diethyl ether; hexane / 0.25 h / 0 - 25 °C 6.1: 94 percent / i-Pr2NEt / CH2Cl2 / 4 h / 25 °C 7.1: 81 percent / LDA / tetrahydrofuran / 12 h / 25 °C 8.1: 99 percent / aq. HCl / propan-2-ol / 4 h / 25 °C 9.1: 95 percent / K2CO3 / acetonitrile / 4 h / Heating 10.1: 52 percent / BCl3 / CH2Cl2 / 1 h / -78 - 25 °C View Scheme

Yield given. Multistep reaction;