반응 #44866

반응 방정식

CH2I2

methyl cyclopentanecarboxylate

HN(iPr)2

n-BuLi

→

title compound

수율 52.0%

Methyl 1-(iodomethyl)cyclopentanecarboxylate

수율 52.0%

용매

THF

THF

반응 조건

후처리

1. 1
   기타with 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
   기타The reaction mixture was quenched with sat. NH4Cl aq. (50 mL)
5. 5
   추출extracted with Et2O (75 mL) for two times
6. 6
   세척the combined organic layer was washed with brine (75 mL)
7. 7
   건조The organic layer was dried over Na2SO4
8. 8
   여과filtered
9. 9
   농축concentrated
10. 10
    기타Removal of the solvent
11. 11
    기타gave a residue, which
12. 12
    기타was chromatographed on a column of silica gel eluting with EtOAc/hexane (1:20→1:10)

실험 절차

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.

출처