Diiodomethane → Methyl 1-(iodomethyl)cyclopentanecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N,N-diisopropylamine (1.31 mL, 9.36 mmol) in tetrahydrofuran (5 mL) was added n-butyllithium (1.58 M in hexane, 5.43 mL, 8.58 mmol) at −10° C. under nitrogen. After being stirred at −10° C. for 1 h, a solution of methyl cyclopentanecarboxylate (1.00 g, 7.80 mmol) in tetrahydrofuran (3 mL) was added dropwise to the mixture, and the mixture was stirred at 0° C. for 2 h. Diiodomethane (0.628 mL, 7.80 mmol) was added to the mixture and the mixture was warmed to room temperature. After being stirred for 16 h, the mixture was quenched with aq. ammonium chloride (50 mL). The mixture was extracted with diethylether (75 mL×2) and washed with brine (75 mL). The organic layer was combined and dried over sodium sulfate and concentrated in vacuo to give an oil. The residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 20:1 to 10:1) to give 1.085 g (52%) of the title compound as a colorless oil.

Provenance & Evidence