Sodium Iodide → methyl 5-iodopentanoate

To a solution of methyl 4-bromovalerate (14 g) in acetone (63 mL), NaI (11.5 g) was added and the mixture was refluxed for 2 hr. It was then cooled to r.t. and the precipitate was filtered. The filtrate was evaporated and ether was added to the residue. The resulting suspension was filtered and the ethereal phase washed with 5% aq NaHSO3 (3×100 mL) and with brine (1×100 mL) and dried over anh. Na2SO4. The solids were filtered and the solvent evaporated to give the crude title compound as a yellow oil (15.85 g).

1. temperaturethe mixture was refluxed for 2 hr
2. filtrationthe precipitate was filtered
3. customThe filtrate was evaporated
4. additionether was added to the residue
5. filtrationThe resulting suspension was filtered
6. washthe ethereal phase washed with 5% aq NaHSO3 (3×100 mL) and with brine (1×100 mL)
7. dry with materialdried over anh. Na2SO4
8. filtrationThe solids were filtered
9. customthe solvent evaporated

ORD record

ord-419f9e67d8fa475783915bab834a1bcb

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07329667B2