反応 #44866

反応方程式

CH2I2

methyl cyclopentanecarboxylate

HN(iPr)2

n-BuLi

→

title compound

収率 52.0%

Methyl 1-(iodomethyl)cyclopentanecarboxylate

収率 52.0%

溶媒

THF

THF

反応条件

後処理

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

実験手順

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.

出典