ammonia in methanol T=100°C; 48 h;

1: flouride ion / tetrahydrofuran 2: NH3 / methanol / 100 °C View Scheme

1: 43 percent / diethyl ether / -50 °C 2: flouride ion / tetrahydrofuran 3: NH3 / methanol / 100 °C View Scheme

1: 83.6 percent / dimethylsulfoxide, oxalyl chloride / CH2Cl2 / 2 h / -70 °C 2: 17.4 percent / Me3Al, 2,4,6-tri-tert-butylphenol / hexane; toluene; diethyl ether / 1.5 h / -78 °C 3: 94.5 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.33 h 4: 95.6 percent / NH3 / methanol / 48 h / 100 °C View Scheme

1: 93 percent / 4-dimethylaminopyridine / acetonitrile / 1 h / Ambient temperature 2: thionyl chloride, N,N-dimethylformamide / CHCl3 / 6.5 h / Heating 3: ethanol / 1.) 1 h, room temp. 2.) 2 h, reflux 4: 86.3 percent / pyridine / 1.) 0 deg C, 2 h, 2.) 3 h, room temp. 5: 83.6 percent / dimethylsulfoxide, oxalyl chloride / CH2Cl2 / 2 h / -70 °C 6: 17.4 percent / Me3Al, 2,4,6-tri-tert-butylphenol / hexane; toluene; diethyl ether / 1.5 h / -78 °C 7: 94.5 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.33 h 8: 95.6 percent / NH3 / methanol / 48 h / 100 °C View Scheme

1: ethanol / 1.) 1 h, room temp. 2.) 2 h, reflux 2: 86.3 percent / pyridine / 1.) 0 deg C, 2 h, 2.) 3 h, room temp. 3: 83.6 percent / dimethylsulfoxide, oxalyl chloride / CH2Cl2 / 2 h / -70 °C 4: 17.4 percent / Me3Al, 2,4,6-tri-tert-butylphenol / hexane; toluene; diethyl ether / 1.5 h / -78 °C 5: 94.5 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.33 h 6: 95.6 percent / NH3 / methanol / 48 h / 100 °C View Scheme

1: 86.3 percent / pyridine / 1.) 0 deg C, 2 h, 2.) 3 h, room temp. 2: 83.6 percent / dimethylsulfoxide, oxalyl chloride / CH2Cl2 / 2 h / -70 °C 3: 17.4 percent / Me3Al, 2,4,6-tri-tert-butylphenol / hexane; toluene; diethyl ether / 1.5 h / -78 °C 4: 94.5 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.33 h 5: 95.6 percent / NH3 / methanol / 48 h / 100 °C View Scheme

1: thionyl chloride, N,N-dimethylformamide / CHCl3 / 6.5 h / Heating 2: ethanol / 1.) 1 h, room temp. 2.) 2 h, reflux 3: 86.3 percent / pyridine / 1.) 0 deg C, 2 h, 2.) 3 h, room temp. 4: 83.6 percent / dimethylsulfoxide, oxalyl chloride / CH2Cl2 / 2 h / -70 °C 5: 17.4 percent / Me3Al, 2,4,6-tri-tert-butylphenol / hexane; toluene; diethyl ether / 1.5 h / -78 °C 6: 94.5 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.33 h 7: 95.6 percent / NH3 / methanol / 48 h / 100 °C View Scheme

Multistep reaction;

1: 87 percent / CH3ONa; methanol / 20 °C View Scheme