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

HRID 967615Notes

Reaction equation

HRID 967615 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-2c04621f6c874692b048da5f311e33b1
Source dataset
uspto-grants-2005_10
Patent number
US06953812B2

Reaction notes

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