sodium methylate in methanol T=-35°C; 0.5 h;

1: 96 percent / NaOH / methanol / 3 h / Ambient temperature 2: 1.) ethyl chloroformate, triethylamine, 2.) sodium borohydride, tetra-n-butylammonium bromide / 1.) CH2Cl2, -40 deg C, 40 min, 2.) water, CH2Cl2, -10 deg C, 1 h 3: 86 percent / dimethylformamide / 3.75 h / 65 °C 4: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 4 h / Ambient temperature 5: 69 percent / sodium methoxide / methanol / 0.5 h / -35 °C View Scheme

1: 1.) ethyl chloroformate, triethylamine, 2.) sodium borohydride, tetra-n-butylammonium bromide / 1.) CH2Cl2, -40 deg C, 40 min, 2.) water, CH2Cl2, -10 deg C, 1 h 2: 86 percent / dimethylformamide / 3.75 h / 65 °C 3: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 4 h / Ambient temperature 4: 69 percent / sodium methoxide / methanol / 0.5 h / -35 °C View Scheme

1: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 4 h / Ambient temperature 2: 69 percent / sodium methoxide / methanol / 0.5 h / -35 °C View Scheme

1: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 4 h / Ambient temperature 2: 69 percent / sodium methoxide / methanol / 0.5 h / -35 °C View Scheme

1: 86 percent / dimethylformamide / 3.75 h / 65 °C 2: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 4 h / Ambient temperature 3: 69 percent / sodium methoxide / methanol / 0.5 h / -35 °C View Scheme

1: 96 percent / NaOH / methanol / 3 h / Ambient temperature 2: 1.) ethyl chloroformate, triethylamine, 2.) sodium borohydride, tetra-n-butylammonium bromide / 1.) CH2Cl2, -40 deg C, 40 min, 2.) water, CH2Cl2, -10 deg C, 1 h 3: 86 percent / dimethylformamide / 3.75 h / 65 °C 4: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 4 h / Ambient temperature 5: 69 percent / sodium methoxide / methanol / 0.5 h / -35 °C View Scheme

1: 87 percent / diisopropylethylamine / 4.5 h 2: 72 percent / AlCl3, anisole / CH2Cl2 / 1.5 h / -30 °C View Scheme