sodium hydrogencarbonate

methanol; trimethylamine T=130°C;

T=120°C;

1: 83 percent / LDA / tetrahydrofuran / 1.) -40 deg C, 3 h, 2.) 20 deg C, 12 h 2: 98 percent / 20percent aq. KOH / 48 h / Heating 3: 97 percent / conc. aq. HCl / 1 h / Heating 4: 86 percent / I2 / methanol / 4 h / Heating View Scheme

sodium hydride in benzene