Methyl iodide → dimethyl (2R)-2-methoxybutanedioate

HRID 412416Notes

Reaction equation

HRID 412416 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C@H:4]([OH:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].[CH3:12]I>C(#N)C.[Ag]=O>[CH3:1][O:2][C:3](=[O:11])[C@H:4]([O:10][CH3:12])[CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 110626971,4-dimethyl (2R)-2-hydroxybutanedioate

Product 1

HCID 2192492dimethyl (2R)-2-methoxybutanedioateYield 88%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6342AcetonitrileSolvent

Procedure

The above (R)-2-hydroxysuccinic acid dimethyl ester was re-dissolved in methyl iodide (100 mL), freshly prepared silver oxide (30.2 g) was added and the mixture was stirred for 24 hours at room temperature. The reaction mixture was diluted with acetonitrile (200 mL), and filtered through celite to remove silver salts and excess silver hydroxide. The filtrate was taken to dryness to leave (R)-2-methoxysuccinic acid dimethyl ester as an oil (23.2 g, 88%).

Workup

  1. filtrationfiltered through celite
  2. customto remove silver salts and excess silver hydroxide

Sources & evidence

ORD record
ord-9ab8fd001a5843d8bb1a73e1672cd110
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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