Methyl iodide → HCID 68792437, compound

HRID 1784315Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[H-].[Na+].CI.[C:22](=O)([O-])O.[Na+]>CN(C=O)C.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ethyl 2-(3-chloro-4-nitrophenyl)propanoate (14.1 g) is added dropwise to a suspension of sodium hydride (60% in oil, 2.4 g, 1.1 eq) in DMF (15 ml), cooled down to 0° C. After stirring for 1 hour at this temperature, a solution of methyl iodide (3.72 ml, 1.1 eq) in DMF (40 ml) is added dropwise to the mixture. Stirring is continued for 3 hours at ambient temperature. The reaction medium is cooled down to 0° C. then ethyl acetate, water saturated with sodium hydrogen carbonate are added dropwise, then water. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 and concentrated under reduced pressure in order to produce the expected compound in the form of an oil which crystallizes. The crystals are washed with heptane and dried (13.8 g; 94% yield).

Workup

stirringStirring
waitis continued for 3 hours at ambient temperature
temperatureThe reaction medium is cooled down to 0° C.
extractionAfter decantation and extractions
washthe combined organic phases are washed with salt water
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure in order

Sources & evidence

ORD record: ord-0166efd653fb481392f5e56021c292a9
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501525B2

Reaction notes

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