反应 #44866

反应方程式

CH2I2

methyl cyclopentanecarboxylate

HN(iPr)2

n-BuLi

→

title compound

收率 52.0%

Methyl 1-(iodomethyl)cyclopentanecarboxylate

收率 52.0%

溶剂

THF

THF

反应条件

后处理

1. 1
   其他with 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
   其他The reaction mixture was quenched with sat. NH4Cl aq. (50 mL)
5. 5
   萃取extracted with Et2O (75 mL) for two times
6. 6
   洗涤the combined organic layer was washed with brine (75 mL)
7. 7
   干燥The organic layer was dried over Na2SO4
8. 8
   过滤filtered
9. 9
   浓缩concentrated
10. 10
    其他Removal of the solvent
11. 11
    其他gave a residue, which
12. 12
    其他was chromatographed on a column of silica gel eluting with EtOAc/hexane (1:20→1:10)

实验过程

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.

来源