Diiodomethane → Methyl 1-(iodomethyl)cyclopentanecarboxylate

Temperature

-10 °C

To a stirred solution of HN(iPr)2 (1.31 mL, 9.36 mmol) in THF (5 mL) was added n-BuLi (1.58 M in hexane, 5.43 mL, 8.58 mmol) with keeping −10° C. under N2, and the mixture was stirred at −10° C. for 1 h. Then, to this mixture was added a solution of methyl cyclopentanecarboxylate (1.00 g, 7.80 mmol) in THF (3 mL) dropwise at 0° C., and the mixture was stirred at 0° C. for 2 h. Finally, to this mixture was added CH2I2 (0.628 mL, 7.80 mmol) at 0° C., and the resulting mixture was stirred at room temperature for 16 h. The reaction mixture was quenched with sat. NH4Cl aq. (50 mL), extracted with Et2O (75 mL) for two times, and the combined organic layer was washed with brine (75 mL). The organic layer was dried over Na2SO4, filtered and concentrated. Removal of the solvent gave a residue, which was chromatographed on a column of silica gel eluting with EtOAc/hexane (1:20→1:10) to give 1.085 g (52%) of title compound as a colorless oil.

1. customwith keeping −10° C. under N2
2. stirringthe mixture was stirred at 0° C. for 2 h
3. stirringthe resulting mixture was stirred at room temperature for 16 h
4. customThe reaction mixture was quenched with sat. NH4Cl aq. (50 mL)
5. extractionextracted with Et2O (75 mL) for two times
6. washthe combined organic layer was washed with brine (75 mL)
7. dry with materialThe organic layer was dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customRemoval of the solvent
11. customgave a residue, which
12. customwas chromatographed on a column of silica gel eluting with EtOAc/hexane (1:20→1:10)

ORD record

ord-b47416ae4dd2425e87afdfa132e71e74

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07737163B2