2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran T=0°C; 1 h;

sodium hydride in dichloromethane; N,N-dimethyl-formamide 4 h; Ambient temperature;

1: 60 percent / xylene / 1 h / Heating 2: 76 percent / NaBH4 / methanol / 0.5 h / 0 °C 3: 96 percent / pyridine / 3 h / Ambient temperature 4: 93 percent / NaH / CH2Cl2; dimethylformamide / 4 h / Ambient temperature View Scheme

1: 61 percent / trimethylsilyl triflate / acetonitrile / 20 h / 30 - 35 °C 2: 28 percent / mesityl bromide, Mg / tetrahydrofuran / 1 h / 0 °C View Scheme

1: 76 percent / NaBH4 / methanol / 0.5 h / 0 °C 2: 96 percent / pyridine / 3 h / Ambient temperature 3: 93 percent / NaH / CH2Cl2; dimethylformamide / 4 h / Ambient temperature View Scheme

1: 96 percent / pyridine / 3 h / Ambient temperature 2: 93 percent / NaH / CH2Cl2; dimethylformamide / 4 h / Ambient temperature View Scheme