1-Bromopentane → HCID 22468244, compound

To a stirring solution of diethylmalonate (8.0 g, 50 mmol) in THF (100 mL, 0.5 M) was added sodium hydride (1.2 g, 50 mmol). The solution began bubbling and an exothermic reaction occurred. The reaction eventually turned clear and then pentyl bromide (6.2 mL, 50 mmol) was added. The reaction was refluxed for 20 hours and then cooled to room temperature. Another equivalent of NaH (1.2 g, 50 mmol) was added to the cloudy white mixture which was then stirred for 4 hours at room temperature. Another equivalent of pentyl bromide (6.2 mL, 50 mmol) was added and the reaction was refluxed for 20 hours. The reaction was cooled to room temperature and filtered to remove the precipitated sodium bromide. The mother liquor was collected and concentrated in vacuo to a yellow oil. The crude product was then distilled under vacuum (140° C.) to afford 9.34 g (62%) of pure product.

1. customThe solution began bubbling
2. customan exothermic reaction
3. customThe reaction eventually turned clear
4. temperatureThe reaction was refluxed for 20 hours
5. temperaturethe reaction was refluxed for 20 hours
6. temperatureThe reaction was cooled to room temperature
7. filtrationfiltered
8. customto remove the precipitated sodium bromide
9. customThe mother liquor was collected
10. concentrationconcentrated in vacuo to a yellow oil
11. distillationThe crude product was then distilled under vacuum (140° C.)

ORD record

ord-28b393fe14de430fa1896f591f3c5088

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06384279B1