dimethylammonium chloride; acetic acid; N-ethyl-N,N-diisopropylamine in tetrahydrofuran; water T=120°C; 1 h; Inert atmosphere;

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -55 °C / Inert atmosphere 1.2: 0.25 h / -55 °C / Inert atmosphere 2.1: dimethylammonium chloride / water / 24 h / 70 °C / Inert atmosphere View Scheme

1: 94 percent / NaH / tetrahydrofuran / 16 h / 20 °C 2: 77 percent / p-TsOH / H2O / 1 h / Heating 3: 94 percent / pyridine / 4 h / 0 °C 4: 92 percent / Et3N / CH2Cl2 / 4 h / -78 °C / is allowed to warm to 20 deg C 5: 65 percent / Me3SiCN / acetonitrile / 39 h / 90 °C 6: DIBAH / toluene / 4.5 h / from -78 deg C to 20 deg C 7: 20percent aqu.sodium, potassium tartrate / 5 h / 20 °C View Scheme

formaldehyd

1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane T=20°C; 22 h; Inert atmosphere;

1: 65 percent / Me3SiCN / acetonitrile / 39 h / 90 °C 2: DIBAH / toluene / 4.5 h / from -78 deg C to 20 deg C 3: 20percent aqu.sodium, potassium tartrate / 5 h / 20 °C View Scheme

sodium; L-tartaric acid dipotassium salt T=20°C; 5 h; Yield given;

lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 0.5 h; Inert atmosphere;