Methyl iodide → HCID 19926461, compound

HRID 1647165Notes

Reaction equation

HRID 1647165 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11](=[O:12])[CH:10]=[CH:9][O:8][C:7]=1[CH3:13].[OH-].[K+].[CH3:16]I>>[CH3:16][O:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11](=[O:12])[CH:10]=[CH:9][O:8][C:7]=1[CH3:13]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 104649893-(3-Hydroxypropoxy)-2-methyl-4H-pyran-4-one

Product 1

HCID 19926461HCID 19926461, compoundYield 20.6%

Procedure

A mixture of 3-(3-hydroxy-1-propoxy)-2-methyl-4-pyrone {1.4 g, 7.6 mmol), 85% KOH (0.55 g, 8.4 mmol) and methyliodide (11 g, 76 mmol) was stirred at room temperature for one day. The red solution was partitioned between methylene chloride and half saturated aqueous ammoniumchloride solution. The organic phase was washed with water, dried over Na2SO4 and evaporated. The residue was purified by chromatography on silica gel with methanol/methylene chloride (3:97) as eluent. Removing the eluent by film evaporation afforded 0.31 g (20%) of the desired product as an oil.

Workup

  1. customThe red solution was partitioned between methylene chloride and half saturated aqueous ammoniumchloride solution
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel with methanol/methylene chloride (3:97) as eluent
  6. customRemoving the eluent
  7. customby film evaporation

Sources & evidence

ORD record
ord-9cc9654cd47f495994330c1bdeb041e4
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

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