18-crown-6 ether; potassium carbonate in acetone 12 h; Heating;

1: K3PO4; Pd(PPh3)4 / 1,2-dimethoxy-ethane / 48 h / Heating 2: p-TSA / ethanol; CH2Cl2 / 20 °C 3: 15 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 4: 69 percent / K2CO3; 18-crown-6 / acetone / 12 h / Heating View Scheme

1: 92 percent / iPr2NEt / tetrahydrofuran / 1 h / 20 °C 2: K3PO4; Pd(PPh3)4 / 1,2-dimethoxy-ethane / 48 h / Heating 3: p-TSA / ethanol; CH2Cl2 / 20 °C 4: 15 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 5: 69 percent / K2CO3; 18-crown-6 / acetone / 12 h / Heating View Scheme

1: K3PO4; Pd(PPh3)4 / 1,2-dimethoxy-ethane / 48 h / Heating 2: p-TSA / ethanol; CH2Cl2 / 20 °C 3: 15 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 4: 69 percent / K2CO3; 18-crown-6 / acetone / 12 h / Heating View Scheme