1: Trimethylene glycol With sodium hydride in N,N-dimethyl-formamide; oil T=0 - 20°C; 0.166667 h; 2: n-hexadecyl bromide With potassium iodide in N,N-dimethyl-formamide; oil T=95°C; 4 h;

1: Trimethylene glycol With sodium hydride in N,N-dimethyl-formamide; mineral oil T=20°C; 0.5 h; 2: n-hexadecyl p-toluenesulfonate in N,N-dimethyl-formamide; mineral oil T=80°C;

1: Trimethylene glycol With sodium hydride in 1-methyl-pyrrolidin-2-one; mineral oil T=-5 - 20°C; Industry scaleInert atmosphere; 2: n-hexadecyl methanesulfonate in 1-methyl-pyrrolidin-2-one; mineral oil T=20 - 55°C; Industry scaleInert atmosphere; Product distribution / selectivity;

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -5 - 30 °C / Inert atmosphere; Industry scale 2.1: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / -5 - 20 °C / Industry scale; Inert atmosphere 2.2: 20 - 55 °C / Industry scale; Inert atmosphere View Scheme

1.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 3 h / 90 °C 2.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 20 °C 2.2: 28 h / 20 °C View Scheme