Reaction #1483063

Reaction equation

( 30 )

7-Hydroxy-hept-5-ynoic acid methyl ester

triphenylphosphine

imidazole

iodine

→

propargyl iodide

Yield 83.0%

7-Iodo-hept-5-ynoic acid methyl ester

Yield 83.0%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Washrinsing with 5 mL dichloromethane
2. 2
   Otherthe dichloromethane was evaporated in vacuo to about 2 mL
3. 3
   Filtrationthe resulting mixture filtered through basic alumina
4. 4
   Washwashing with 10% ethyl acetate/hexanes
5. 5
   OtherPurification by flash chromatography on silica gel (10% ethyl acetate/hexanes)

Procedure

A solution of (30) (1.347 g, 8.6 mmol) in 5 mL dichloromethane was added to a mixture of triphenylphosphine (2.725 g, 10.4 mmol), imidazole (726 mg, 10.7 mmol), and iodine (2.602 g, 10.3 mmol) in 34 mL dichloromethane, rinsing with 5 mL dichloromethane. After 40 minutes, the dichloromethane was evaporated in vacuo to about 2 mL and the resulting mixture filtered through basic alumina, washing with 10% ethyl acetate/hexanes. Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes) gave 1.878 g (7.1 mmol, 83%) of the propargyl iodide.

Source