ammonium chloride; iodine; magnesium in tetrahydrofuran

magnesium in diethyl ether

1: 41 percent / CuI, TMSCl / tetrahydrofuran / 1 h / -78 °C 2: Bu4NF / tetrahydrofuran / 0.33 h / 0 °C 3: NaBH4 / ethanol / 21 h / Ambient temperature 4: 89 percent / p-TsOH / benzene / 3 h / Heating 5: 1) LDA / 1) THF, 0.5 h, 2) THF, -78 to -20 deg C, 20 h 6: 0.081 g / BBr3 / CH2Cl2 / 38 h / 0 °C View Scheme

1: 81 percent / CuCN / tetrahydrofuran / 2 h / -18 °C 2: O3; pyridine / propan-2-ol 3: NaBH4 4: Bu4NF 5: aq. KIO4 / ethanol 6: 95 percent / PCC; NaOAc View Scheme

1: diethyl ether / 1 h 2: H2, HClO4 / ethyl acetate View Scheme

48 h; Heating;

tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=20°C; 24 h;