Reaction #59103

Reaction equation

triphenylphosphine

triethylamine

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

allyl alcohol

triethylborane

lithium chloride

→

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

Solvents

THF

sodium bicarbonate

THF

Conditions

Workup

1. 1
   Otherat room temperature
2. 2
   Extractionextracted with ethyl acetate
3. 3
   WashOrganics were washed with brine
4. 4
   Dryingdried with sodium sulfate
5. 5
   Concentrationconcentrated
6. 6
   OtherCrude product was purified

Procedure

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.

Source