N-hexadecyl-N,N,N-trimethylammonium bromide; trichlorophosphate in acetonitrile Vilsmeier-Haack cyclisation; 1.41667 h; Heating;

trichlorophosphate T=100°C; 2 h; further temperature;

trichlorophosphate T=60°C; 16 h;

trichlorophosphate T=75°C; 16.5 h;

1: acetic acid / |Reflux 2: trichlorophosphate / 24 h / 85 °C View Scheme

trichlorophosphate

ammonia; iodine in tetrahydrofuran; water

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C 1.2: 2 h 2.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / 0 - 20 °C 2.2: 4 h 3.1: methanol / 8 h / 80 °C 4.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.67 h / -20 °C / Molecular sieve 4.2: 4 h / -20 °C 5.1: copper (I) cyanide / tetrahydrofuran; diethyl ether / 1 h / -40 °C 5.2: 3 h / -40 °C 5.3: 3 h 6.1: / dichloromethane / 1 h / 0 - 20 °C 7.1: diethyl ether / 1 h / 0 °C 8.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C 9.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C 9.2: 0.5 h 10.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C 11.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C 12.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 13.1: tetrahydrofuran / 24 h / 45 °C View Scheme

1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran T=20°C; 1 h;

1: ethanol; sodium tetrahydroborate / 0.67 h / 0 - 20 °C 2: thionyl chloride / dichloromethane / 2.5 h / 20 °C View Scheme