Реакция #59103

Уравнение реакции

triphenylphosphine

triethylamine

2-(2-fluoro-5-nitrophenyl) propanal

allyl alcohol

triethylborane

lithium chloride

→

2-(2-fluoro-5-nitrophenyl)-2-methylpent-4-enal

Растворители

THF

sodium bicarbonate

THF

Условия реакции

Обработка

1. 1
   Другоеat room temperature
2. 2
   Экстракцияextracted with ethyl acetate
3. 3
   ПромывкаOrganics were washed with brine
4. 4
   Сушкаdried with sodium sulfate
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеCrude product was purified

Методика

To a solution of palladium acetate (0.1 eq), triphenylphosphine (0.2 eq), lithium chloride (1.0 eq) in THF were sequentially added 2-(2-fluoro-5-nitrophenyl) propanal (1.1 eq) in THF, allyl alcohol (1.0 eq), triethylamine (1.2 eq) and triethylborane (2.4 eq) under nitrogen at room temperature. Solution was allowed to stir for 2 h. Mixture was diluted with saturated solution of sodium bicarbonate, extracted with ethyl acetate. Organics were washed with brine, dried with sodium sulfate and concentrated. Crude product was purified using flash chromatography (85% Hex: 15% EtoAc) on silica to afford 2-(2-fluoro-5-nitrophenyl)-2-methylpent-4-enal.

Источник