Methyl iodide → HCID 68792437, compound
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
Reactant 4
Product 1
Reagents, catalysts & solvents 3
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, then water are added dropwise. 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-d4ba9d9749c6409bb451b1b225b2c51c
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08227485B2
Reaction notes
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