Methyl iodide → HCID 54178108, compound

HRID 487008Notes

Reaction equation

HRID 487008 reaction equation
[CH3:1][O:2][CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].[CH3:16]I>C1OCCOCCOCCOCCOC1.CN(C)C=O>[CH3:1][O:2][C:3]([CH3:16])([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 575727Diethyl methoxymalonate

Product 1

HCID 54178108HCID 54178108, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 3633615-Crown-5CatalystHCID 6228DimethylformamideSolvent

Procedure

Diethyl methoxymalonate (31.0 grams, 0.2 mole), prepared in Example LIII Part A, sodium hydride (3.91 grams of 60% reagent, 0.2 mole), methyl iodide (46.27 grams, 0.3 mole) and 15-crown-5 (2 drops) were reacted in 300 millilaters of N,N-dimethylformamide in a manner similar to that described in Example LII Part A to give 23.77 grams (0.1 mole) of diethyl methoxy(methyl)malonate. NMR analysis of the product indicated the following:

Sources & evidence

ORD record
ord-86f92586158f4484ac1150fc924bdc61
Source dataset
uspto-grants-1994_03
Patent number
US05292937

Reaction notes

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