Sodium Iodide → (R)-5-acetoxy-1-iodohexane

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.

1. customfitted with magnetic stirrer bar and a reflux condenser
2. temperaturerefluxed for 12 h
3. customAcetone was removed under reduced pressure
4. customThe crude product was partitioned between 60 ml ethyl acetate and 60 ml water layer
5. washThe organic layer was washed with 10% sodium thiosulphate solution
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure

ORD record

ord-b7263f1b9cfd405db9f1e93e925472af

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06469017B1