Reaction #7424

Reaction equation

Diethylazodicarboxylate

5-norbornene-2-methanol

4-iodophenol

triphenylphosphine

→

8

Yield 97.0%

5-[[(p-iodophenyl)oxy]methyl]bicyclo[2.2.1]hept-2-ene

Yield 97.0%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONAfter completion of the addition
2. 2
   OtherThe solvent was removed under reduced pressure
3. 3
   Extractionthe oily residue was extracted three times with hot hexane
4. 4
   OtherCombined hexane extracts were evaporated under reduced pressure

Procedure

Diethylazodicarboxylate (8.7 g) was added dropwise to a solution of 5-norbornene-2-methanol (6.2 g, 0.05 mol), 4-iodophenol (11.0 g, 0.05 mol) and triphenylphosphine (13.1 g, 0.05 mol) in 100 mL of anhydrous tetrahydrofuran. After completion of the addition, the resulting solution was stirred for 18 h at room temperature. The solvent was removed under reduced pressure and the oily residue was extracted three times with hot hexane. Combined hexane extracts were evaporated under reduced pressure to give 8 (15.0 g, 97%) as a colorless oil.

Source