Reaktion #59103

Reaktionsgleichung

triphenylphosphine

triethylamine

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

allyl alcohol

triethylborane

lithium chloride

→

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

Lösungsmittel

THF

sodium bicarbonate

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat room temperature
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenOrganics were washed with brine
4. 4
   Trocknendried with sodium sulfate
5. 5
   Einengenconcentrated
6. 6
   SonstigeCrude product was purified

Vorschrift

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.

Quelle