Methyl iodide → HCID 14459623, compound

HRID 1670002Notes

Reaction equation

HRID 1670002 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[C:5]([CH3:9])([CH3:8])[CH2:6][OH:7])[CH3:2].[CH3:11]I>CC#N>[CH2:1]([O:3][C:4](=[O:10])[C:5]([CH3:9])([CH3:8])[CH2:6][O:7][CH3:11])[CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 274432ethyl 3-hydroxy-2,2-dimethylpropanoate

Product 1

HCID 14459623HCID 14459623, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,2-dimethyl-3-hydroxypropionic acid ethyl ester (1.3 g, 10.0 mmol) in CH3CN (30 mL) was added Ag2O (11.5 g, 50.0 mmol) and methyl iodide (0.56 mL, 11 mmol). The reaction mixture was stirred at rt for 12 h and quenched with a saturated aqueous NH4Cl. The mixture was filtered though Celite, the filtrate concentrated in vacuo, and the residue was purified by column chromatography (EtOAc/Hex=1/10) to give the title compound (1.34 g, 91.2%).

Workup

  1. customquenched with a saturated aqueous NH4Cl
  2. filtrationThe mixture was filtered though Celite
  3. concentrationthe filtrate concentrated in vacuo
  4. customthe residue was purified by column chromatography (EtOAc/Hex=1/10)

Sources & evidence

ORD record
ord-cdfcf32aff634e2f8bebb7b3d031abea
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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