Methyl iodide → Dimethyl 3-methoxypentanedioate

HRID 472971Notes

Reaction equation

HRID 472971 reaction equation
[OH:1][CH:2]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5].I[CH3:14]>CN(C=O)C>[CH3:14][O:1][CH:2]([CH2:3][C:4]([O:6][CH3:7])=[O:5])[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 232491Dimethyl 3-hydroxypentanedioate

Product 1

HCID 14670803Dimethyl 3-methoxypentanedioateYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of dimethyl 3-hydroxypentanedioate (9 g, 51.1 mmol) in DMF (70 mL) was added Ag2O (35.5 g, 154.3 mmol) and iodomethane (48.2 g, 339.2 mmol) under ice-cooling. The mixture was stirred at room temperature overnight. The mixture was filtrated and the filtrate was washed with water. Ether was added and the organic layer was dried and concentrated to give the crude product, which was purified by column chromatography to give dimethyl 3-methoxypentanedioate (8 g, 82%). 1H-NMR (CDCl3): 2.48 (m, 4H), 3.21 (m, 3H), 3.50 (m, 6H), 3.85 (s, 1H).

Workup

  1. temperaturecooling
  2. filtrationThe mixture was filtrated
  3. washthe filtrate was washed with water
  4. additionEther was added
  5. customthe organic layer was dried
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-130f376b32c649c4a2afde6e404a330f
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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