4-toluenesulfonyl azide; triethylamine in acetonitrile 10 h; Ambient temperature;

triethylamine

1: NaH 2: TsN3 View Scheme

1: 1) NaH; 2) n-BuLi / 1) THF, 0 deg C, 15 min; 2) hexane, 0 deg C, 15 min; 3) THF, 5-10 deg C, 45 min 2: 98 percent / triethylamine, tosyl azide / acetonitrile / 10 h / Ambient temperature View Scheme

1: 1) NaH; 2) n-BuLi / 1) THF, 0 deg C, 15 min; 2) hexane, 0 deg C, 15 min; 3) THF, 5-10 deg C, 45 min 2: 98 percent / triethylamine, tosyl azide / acetonitrile / 10 h / Ambient temperature View Scheme