Reacción #330064

Ecuación de reacción

2-(1-Azidoethyl)-3-phenylbenzo[b]thiophene

triphenylphosphine

triphenylphosphine

→

title compound

Rendimiento 83.1%

1-(3-Phenylbenzo[b]thiophen-2-yl)ethylamine

Rendimiento 83.1%

Disolventes

THF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONadded
2. 2
   workup.STIRRINGThe reaction mixture was stirred at RT for 1 h
3. 3
   Lavadowashed with MeOH
4. 4
   Lavadothe product eluted with 2M NH3/MeOH
5. 5
   workup.ADDITIONThe product containing fractions
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% MeOH in DCM)

Procedimiento

2-(1-Azidoethyl)-3-phenylbenzo[b]thiophene (211 mg, 0.76 mmol) was dissolved in a mixture THF (4 mL) and water (0.27 mL) and triphenylphosphine (237 mg, 0.91 mmol) added. The mixture was stirred at RT for 1 h then additional triphenylphosphine (237 mg) was added. The reaction mixture was stirred at RT for 1 h then the reaction mixture was loaded onto an Isolute® SCX-2 cartridge and washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% MeOH in DCM) affording the title compound as a white solid (160 mg, 83%). 1H NMR (CDCl3, 400 MHz): δ 7.84 (1H, dd, J=7.63, 1.55 Hz), 7.52-7.27 (8H, m), 4.56-4.44 (1H, br), 1.76 (2H, s), 1.47 (3H, d, J=6.21 Hz).

Fuente