1: With n-butyllithium; boric acid trimethyl ester in tetrahydrofuran 2: With dihydrogen peroxide; acetic acid T=0 - 20°C;

1.1: 96 percent / NaH / diethyl ether; dimethylformamide / 0 - 20 °C 2.1: n-BuLi; B(OMe)3 / tetrahydrofuran 2.2: 95 percent / AcOH; H2O2 / 0 - 20 °C View Scheme

1: With sodium hydride in diethyl ether; N,N-dimethyl-formamide 2: With n-butyllithium; boric acid trimethyl ester in tetrahydrofuran 3: With dihydrogen peroxide; acetic acid in tetrahydrofuran

sodium hydroxide in tetrahydrofuran T=20°C; 4 h;

1: 91 percent / MCPBA / CHCl3 / 24 h / 20 °C 2: 59 percent / aq. NaOH / tetrahydrofuran / 4 h / 20 °C View Scheme

1.1: 97 percent / LiCl; 3 Angstroem molecular sieves / toluene; various solvent(s) / 24 h / 20 °C 2.1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 3.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C 4.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C 5.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 6.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 7.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 8.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 9.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 10.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 11.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 12.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 13.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 14.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 15.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 16.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 17.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 18.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 19.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 20.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 21.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 22.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 22.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 22.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 23.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 24.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme

1: 96 percent / K2CO3 / acetone / 48 h / 20 °C 2: 73 percent / NaI; HCl / acetone; methanol / 4 h View Scheme

chloro-trimethyl-silane; sodium iodide in acetonitrile Substitution;