Methyl iodide → Methyl 2-(4-chlorophenyl)-2-cyclopentylpropanoate

HRID 12299Notes

Reaction equation

[CH:1](NC(C)C)(C)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=1.CI>C1COCC1.C([Li])CCC.[Cl-].[NH4+]>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)([CH3:1])[C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: -35 °C

Procedure

To a solution of diisopropylamine (0.15 ml) in THF (2 ml), n-butyl lithium (1.5 M hexane solution, 0.6 ml) was added at −78° C., stirred for 10 minutes and another solution of methyl 2-(4-chlorophenyl)-2-cyclopentylacetate (200 mg) in THF (1.5 ml) was added dropwise. After 15 minutes' stirring, the system temperature was raised to −35° C., and methyl iodide (0.15 ml) was added. The reaction liquid temperature was raised to 0° C., and the liquid was stirred for 1.5 hours, diluted with saturated aqueous ammonium chloride solution and extracted with diethyl ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and condensed under reduced pressure. The resulting residue was purified on silica gel column chromatography (hexane/ethyl acetate 60/1) to provide methyl 2-(4-chlorophenyl)-2-cyclopentylpropionate (180 mg) as yellow oily substance.

Workup

stirringAfter 15 minutes' stirring
customThe reaction liquid temperature
temperaturewas raised to 0° C.
stirringthe liquid was stirred for 1.5 hours
extractionextracted with diethyl ether
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate and condensed under reduced pressure
customThe resulting residue was purified on silica gel column chromatography (hexane/ethyl acetate 60/1)

Sources & evidence

ORD record: ord-605b849843804862a90b8e36f41a45f4
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727998B2

Reaction notes

Loading…