Sodium Iodide → (R)-5-acetoxy-1-iodohexane
Reaction equation
[C:1]([O:4][C@H:5]([CH3:11])[CH2:6][CH2:7][CH2:8][CH2:9]Cl)(=[O:3])[CH3:2].[I-:12].[Na+]>>[C:1]([O:4][C@H:5]([CH3:11])[CH2:6][CH2:7][CH2:8][CH2:9][I:12])(=[O:3])[CH3:2]Participants
3
Procedure
A solution of 4.80 g (R)-5-acetoxy-1-chlorohexane (26.89 mmol) (prepared in accordance with procedures set forth in U.S. Pat. No. 5,629,423) was added to 5.39 g sodium iodide (36 mmol) in a round bottomed flask fitted with magnetic stirrer bar and a reflux condenser and refluxed for 12 h with stirring. Acetone was removed under reduced pressure. The crude product was partitioned between 60 ml ethyl acetate and 60 ml water layer. The organic layer was washed with 10% sodium thiosulphate solution followed by 20 ml water and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield 7 g (96%) (R)-5-Acetoxy-1-iodohexane.
Workup
- customfitted with magnetic stirrer bar and a reflux condenser