Diiodomethane → Methyl 1-(iodomethyl)cyclopentanecarboxylate

Temperature

-10 °C

To a stirred solution of N,N-diisopropylamine (1.31 mL, 9.36 mmol) in tetrahydrofuran (5 mL) was added n-butyllithium (1.58 M in hexane, 5.43 mL, 8.58 mmol) at −10° C. under nitrogen. After being stirred at −10° C. for 1 h, a solution of methyl cyclopentanecarboxylate (1.00 g, 7.80 mmol) in tetrahydrofuran (3 mL) was added dropwise to the mixture, and the mixture was stirred at 0° C. for 2 h. Diiodomethane (0.628 mL, 7.80 mmol) was added to the mixture and the mixture was warmed to room temperature. After being stirred for 16 h, the mixture was quenched with aq. ammonium chloride (50 mL). The mixture was extracted with diethylether (75 mL×2) and washed with brine (75 mL). The organic layer was combined and dried over sodium sulfate and concentrated in vacuo to give an oil. The residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 20:1 to 10:1) to give 1.085 g (52%) of the title compound as a colorless oil.

1. stirringthe mixture was stirred at 0° C. for 2 h
2. temperaturethe mixture was warmed to room temperature
3. stirringAfter being stirred for 16 h
4. customthe mixture was quenched with aq. ammonium chloride (50 mL)
5. extractionThe mixture was extracted with diethylether (75 mL×2)
6. washwashed with brine (75 mL)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated in vacuo
9. customto give an oil
10. customThe residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 20:1 to 10:1)

ORD record

ord-709bd1ccf22841a6a184d6bac833c024

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08816090B2