Methyl iodide → 2-(4-Allyloxyphenyl)-2-methylpropionic acid methyl ester

HRID 491055Notes

Reaction equation

HRID 491055 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]=[CH2:15])=[CH:8][CH:7]=1)[CH3:5].[H-].[Na+].[CH3:19]I>CN(C)C=O>[CH3:1][O:2][C:3](=[O:16])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH:14]=[CH2:15])=[CH:10][CH:11]=1)([CH3:19])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 685415412-(4-Allyloxyphenyl)-proprionic acid methyl ester

Product 1

HCID 685403022-(4-Allyloxyphenyl)-2-methylpropionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. solution of the product of Example 46B (1.9 g, 8.6 mmol) in anhydrous dimethylformamide (10 mL) was treated portion-wise with 60% sodium hydride (410 mg, 10 mmol) in mineral oil. The reaction mixture was stirred twenty minutes at 0° C., and methyl iodide (1.4 mL, 22 mmol) was then added. Ice bath was removed, and reaction mixture stirred 16 hours at room temperature. Reaction mixture quenched with saturated ammonium chloride, and product extracted with ethyl acetate (2×). The combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. Residue purified by normal phase HPLC on silica gel eluting with 3% ethyl acetate/hexane to provide the title compound.

Workup

  1. customIce bath was removed
  2. customreaction mixture
  3. stirringstirred 16 hours at room temperature
  4. customReaction mixture
  5. customquenched with saturated ammonium chloride, and product
  6. extractionextracted with ethyl acetate (2×)
  7. washThe combined extracts were washed with water and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customResidue purified by normal phase HPLC on silica gel eluting with 3% ethyl acetate/hexane

Sources & evidence

ORD record
ord-778e5bb4f43d44619b20d3d62fb6c237
Source dataset
uspto-grants-2009_05
Patent number
US07528282B2

Reaction notes

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