sodium tetrahydroborate in methanol T=20°C; 0.166667 h;

sodium carbonate in methanol; ethyl acetate; toluene

potassium acetate; palladium diacetate in N,N-dimethyl acetamide T=150°C; 16 h; Inert atmosphere;

1.1: n-BuLi / toluene; hexane; tetrahydrofuran / -50 °C 1.2: triisopropyl borate / toluene; tetrahydrofuran; hexane / -50 - -15 °C 1.3: 73 percent / aq. NaOH / toluene; tetrahydrofuran; hexane 2.1: 91 percent / Pd(PPh3)4; aq. Na2CO3 / 1,2-dimethoxy-ethane / 1 h / 90 °C 3.1: 99 percent / NaBH4 / methanol / 0.17 h / 20 °C View Scheme

1: 91 percent / Pd(PPh3)4; aq. Na2CO3 / 1,2-dimethoxy-ethane / 1 h / 90 °C 2: 99 percent / NaBH4 / methanol / 0.17 h / 20 °C View Scheme

sodium hydrogencarbonate in dichloromethane