Реакция #330035

Уравнение реакции

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

triphenylphosphine

triphenylphosphine

→

1-(3-phenylbenzo[b]thiophen-2-yl)ethanamine

Выход 83.5%

Растворители

THF

water

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGStirring
3. 3
   workup.WAITwas continued for 1 h
4. 4
   Другоеthe crude reaction mixture
5. 5
   Промывкаwas washed with MeOH
6. 6
   Промывкаthe product eluted with 2M NH3/MeOH
7. 7
   workup.ADDITIONThe product containing fractions
8. 8
   Концентрированиеconcentrated under reduced pressure
9. 9
   ДругоеThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% MeOH in DCM)

Методика

2-(1-Azidoethyl)-3-phenylbenzo[b]thiophene (211 mg, 0.756 mmol) was dissolved in a mixture THF (4 mL) and water (0.27 mL) and triphenylphosphine (237 mg, 0.91 mmol) was added. The mixture was stirred at RT for 1 h and then additional triphenylphosphine (237 mg) was added. Stirring was continued for 1 h and the crude reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% MeOH in DCM) affording 1-(3-phenylbenzo[b]thiophen-2-yl)ethanamine 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).

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