1: pyrrole carboxaldehyde With sodium hydride in tetrahydrofuran; mineral oil T=20°C; 0.25 h; 2: p-toluenesulfonyl chloride in tetrahydrofuran; mineral oil T=20°C; 1 h;

sodium hydride 1.) ether, 2.5 h, reflux, 2.) a) 0 deg C, 5 h, b) room temperature, 35 h; Yield given. Multistep reaction;

1.1: 317 mg / zinc borohydride / diethyl ether / 0.5 h / 0 °C 2.1: 87 percent / mesyl chloride; N,N-diisopropylethylamine / CH2Cl2 / 0.83 h / 0 - 20 °C 3.1: methylmagnesium iodide / diethyl ether; tetrahydrofuran / 1 h / -10 - 20 °C 3.2: diethyl ether; tetrahydrofuran / 2 h / -10 - 20 °C 4.1: 99 percent / sodium hydride / tetrahydrofuran / 1 h / 20 °C View Scheme

1.1: 317 mg / zinc borohydride / diethyl ether / 0.5 h / 0 °C 2.1: 87 percent / mesyl chloride; N,N-diisopropylethylamine / CH2Cl2 / 0.83 h / 0 - 20 °C 3.1: methylmagnesium iodide / diethyl ether; tetrahydrofuran / 1 h / -10 - 20 °C 3.2: diethyl ether; tetrahydrofuran / 2 h / -10 - 20 °C View Scheme

1.1: 317 mg / zinc borohydride / diethyl ether / 0.5 h / 0 °C 2.1: 87 percent / mesyl chloride; N,N-diisopropylethylamine / CH2Cl2 / 0.83 h / 0 - 20 °C 3.1: methylmagnesium iodide / diethyl ether; tetrahydrofuran / 1 h / -10 - 20 °C 3.2: 63 percent / diethyl ether; tetrahydrofuran / 2 h / -10 - 20 °C 4.1: 85 percent / aq. NaOH / methanol / 3 h / Heating View Scheme