Reaction #6818

Reaction equation

pent-4-ynoic acid

iodobenzene

→

5-phenylpent-4-ynoic acid

Yield 28.1%

Solvents

diethylamine

Conditions

Workup

1. 1
   OtherThe volatile material are evaporated by a rotary evaporator
2. 2
   workup.DISSOLUTIONthe resulting residue was dissolved in 50 mL dichloromethane
3. 3
   Washwashed with 1 M HCl (50 mL)
4. 4
   DryingThe dichloromethane layer was dried over sodium sulfate
5. 5
   Otherevaporated to dryness under vacuum
6. 6
   OtherThe residue was purified by column chromatography (ethyl acetate/dichloromethane)

Procedure

A solution of pent-4-ynoic acid (1.0 g, 10 mmol), iodobenzene (2.3 ml, 20 mmol), copper(I) iodide (75 mg, 0.40 mmol) and dichlorobis(triphenylphosphine)-platinum(II) (140 mg, 0.20 mmol) in 20 mL of diethylamine was stirred at rt for 3 days. The volatile material are evaporated by a rotary evaporator and the resulting residue was dissolved in 50 mL dichloromethane and washed with 1 M HCl (50 mL). The dichloromethane layer was dried over sodium sulfate and evaporated to dryness under vacuum. The residue was purified by column chromatography (ethyl acetate/dichloromethane) to afford 5-phenylpent-4-ynoic acid (0.49 g).

Source