Cyclopentanol → (4-Bromobutoxy)cyclopentane

Temperature

0 °C

NaH (560 mg, 13.93 mmol, 60% disp. in mineral oil) was washed with hexanes (3×20 mL) in a pressure tube and toluene (6 mL,) was added. The solution was cooled to 0° C. and cyclopentanol (1 g, 11.61 mmol) in toluene (6 mL) was added over 20 min. After stirring at 0° C. for 30 min., 1,4-dibromobutane (1.39 mL, 11.61 mmol) and KI (250 mg) were added. The solution was heated to 100° C. for 14 hours. Upon cooling, the reaction was quenched with NaCl (sat. aq.) and the product extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated. Purification of the residue via flash column chromatography afforded (4-bromobutoxy)cyclopentane.

1. temperatureThe solution was heated to 100° C. for 14 hours
2. temperatureUpon cooling
3. customthe reaction was quenched with NaCl (sat. aq.)
4. extractionthe product extracted with EtOAc
5. dry with materialThe organic layer was dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification of the residue via flash column chromatography

ORD record

ord-57207737ad7f4ef8b1d385da84fca41a

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07452889B2