Реакция #44866

Уравнение реакции

CH2I2

methyl cyclopentanecarboxylate

HN(iPr)2

n-BuLi

→

title compound

Выход 52.0%

Methyl 1-(iodomethyl)cyclopentanecarboxylate

Выход 52.0%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Другоеwith 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
   ДругоеThe reaction mixture was quenched with sat. NH4Cl aq. (50 mL)
5. 5
   Экстракцияextracted with Et2O (75 mL) for two times
6. 6
   Промывкаthe combined organic layer was washed with brine (75 mL)
7. 7
   СушкаThe organic layer was dried over Na2SO4
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated
10. 10
    ДругоеRemoval of the solvent
11. 11
    Другоеgave a residue, which
12. 12
    Другоеwas chromatographed on a column of silica gel eluting with EtOAc/hexane (1:20→1:10)

Методика

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.

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