Reacción #44866

Ecuación de reacción

CH2I2

methyl cyclopentanecarboxylate

HN(iPr)2

n-BuLi

→

title compound

Rendimiento 52.0%

Methyl 1-(iodomethyl)cyclopentanecarboxylate

Rendimiento 52.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowith keeping −10° C. under N2
2. 2
   workup.STIRRINGthe mixture was stirred at 0° C. for 2 h
3. 3
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 16 h
4. 4
   OtroThe reaction mixture was quenched with sat. NH4Cl aq. (50 mL)
5. 5
   Extracciónextracted with Et2O (75 mL) for two times
6. 6
   Lavadothe combined organic layer was washed with brine (75 mL)
7. 7
   SecadoThe organic layer was dried over Na2SO4
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated
10. 10
    OtroRemoval of the solvent
11. 11
    Otrogave a residue, which
12. 12
    Otrowas chromatographed on a column of silica gel eluting with EtOAc/hexane (1:20→1:10)

Procedimiento

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.

Fuente