1.1: pyridine / 10 h / 45 - 50 °C 2.1: NaH / tetrahydrofuran / 1 h / 20 °C 2.2: tetrahydrofuran / 4 h / 50 °C 3.1: p-TsOH; MeOH / CH2Cl2 / 8 h / 20 °C 4.1: pyridine / diethyl ether; tetrahydrofuran / 4 h / Heating 4.2: H2O; pyridine / diethyl ether; tetrahydrofuran / 1 h 5.1: CHCl3; propan-2-ol; various solvent(s) / 5 h / 65 °C View Scheme

1.1: p-TsOH; MeOH / CH2Cl2 / 8 h / 20 °C 2.1: pyridine / diethyl ether; tetrahydrofuran / 4 h / Heating 2.2: H2O; pyridine / diethyl ether; tetrahydrofuran / 1 h 3.1: CHCl3; propan-2-ol; various solvent(s) / 5 h / 65 °C View Scheme

1.1: NaH / tetrahydrofuran / 1 h / 20 °C 1.2: tetrahydrofuran / 4 h / 50 °C 2.1: p-TsOH; MeOH / CH2Cl2 / 8 h / 20 °C 3.1: pyridine / diethyl ether; tetrahydrofuran / 4 h / Heating 3.2: H2O; pyridine / diethyl ether; tetrahydrofuran / 1 h 4.1: CHCl3; propan-2-ol; various solvent(s) / 5 h / 65 °C View Scheme

1.1: pyridine / diethyl ether; tetrahydrofuran / 4 h / Heating 1.2: H2O; pyridine / diethyl ether; tetrahydrofuran / 1 h 2.1: CHCl3; propan-2-ol; various solvent(s) / 5 h / 65 °C View Scheme

1.1: pyridine / dimethylformamide / 2 h 2.1: pyridine / 10 h / 45 - 50 °C 3.1: NaH / tetrahydrofuran / 1 h / 20 °C 3.2: tetrahydrofuran / 4 h / 50 °C 4.1: p-TsOH; MeOH / CH2Cl2 / 8 h / 20 °C 5.1: pyridine / diethyl ether; tetrahydrofuran / 4 h / Heating 5.2: H2O; pyridine / diethyl ether; tetrahydrofuran / 1 h 6.1: CHCl3; propan-2-ol; various solvent(s) / 5 h / 65 °C View Scheme

in chloroform; isopropyl alcohol T=65°C; 5 h;

1: 2-bromoethyl phosphorodichloridate; (+/-)-3-octadecanamido-2-ethoxy-1-propanol Alkylation; 2: trimethylamine With water in chloroform; N,N-dimethyl-formamide; isopropyl alcohol Amination;

triethylamine 1.) benzene, RT, 4 h, 2.) CH3CN, 65 deg C; Yield given. Multistep reaction;