تفاعل #44866

معادلة التفاعل

CH2I2

methyl cyclopentanecarboxylate

HN(iPr)2

n-BuLi

→

title compound

المردود 52.0%

Methyl 1-(iodomethyl)cyclopentanecarboxylate

المردود 52.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىwith 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
   أخرىThe reaction mixture was quenched with sat. NH4Cl aq. (50 mL)
5. 5
   استخلاصextracted with Et2O (75 mL) for two times
6. 6
   غسيلthe combined organic layer was washed with brine (75 mL)
7. 7
   تجفيفThe organic layer was dried over Na2SO4
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated
10. 10
    أخرىRemoval of the solvent
11. 11
    أخرىgave a residue, which
12. 12
    أخرىwas chromatographed on a column of silica gel eluting with EtOAc/hexane (1:20→1:10)

الإجراء التجريبي

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.

المصدر