Реакция #997894

Уравнение реакции

Water

anthracen-9-yl-methanol

(cyanomethyl)trimethylphosphonium iodide

diisopropylethylamine

→

3-anthracen-9-yl-propionitrile

Выход 95.0%

Растворители

propionitrile

Условия реакции

Обработка

1. 1
   Другоеnitrogen was bubbled though the mixture
2. 2
   workup.STIRRINGthe mixture was stirred for 20 hours
3. 3
   workup.ADDITIONWater (480 mL) and concentrated HCl (19 mL) were added
4. 4
   Экстракцияthe mixture was extracted with EtOAc
5. 5
   ПромывкаThe organic layer was washed with brine
6. 6
   Сушкаdried over MgSO4
7. 7
   Концентрированиеconcentrated
8. 8
   ДругоеThe resulting solid was purified by silica gel column chromatography (hexane:CHCl3=1:1)

Методика

To a solution of anthracen-9-yl-methanol (6.58 g, 31.6 mmol) and (cyanomethyl)trimethylphosphonium iodide (19.19 g, 78.96 mmol) in propionitrile (77 mL) was added diisopropylethylamine (DIPEA, 49.4 mL, 94.74 mmol) and the mixture was stirred at 97° C. for 20 hours. Water (3.82 mL) was added, nitrogen was bubbled though the mixture, and the mixture was stirred for 20 hours. Water (480 mL) and concentrated HCl (19 mL) were added and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated. The resulting solid was purified by silica gel column chromatography (hexane:CHCl3=1:1) to give 3-anthracen-9-yl-propionitrile as brown crystals (6.93 g, 95% yield). 1H NMR (CDCl3) δ 8.43 (1H, s), 8.19 (2H, d), 8.05 (2H, d), 7.60 (2H, dd), 7.51 (2H, dd), 4.02 (2H, t), 2.79 (2H, t).

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