Iodoethane → 3-Ethoxy-2-methyl-4H-pyran-4-one

HRID 912653Notes

Reaction equation

HRID 912653 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][C:3]=1[CH3:9].[OH-].[Na+].[CH2:12](I)[CH3:13]>CO.O>[CH2:12]([O:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][C:3]=1[CH3:9])[CH3:13]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 8369MaltolHCID 14798Sodium Hydroxide

Product 1

HCID 98340133-Ethoxy-2-methyl-4H-pyran-4-oneYield 71.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-Hydroxy-2-methyl-4-pyrone (10 g, 79.4 mmol) was dissolved in methanol (10 mL) and sodium hydroxide (3.49 g, 87.3 mmol) in water (8 mL) was added, followed by ethyl iodide (6.97 mL, 87.3 mmol). The reaction mixture was stirred under reflux overnight. The reaction mixture was then partitioned between water (50 mL) and CH2Cl2 (100 mL). The organic phase was washed with sodium hydroxide (5%, aq.), water, dried (MgSO4) and evaporated to give the title product (8.7 g, 71%) as a solid. The crude product was used in the next step without further purification.

Workup

  1. temperatureunder reflux overnight
  2. customThe reaction mixture was then partitioned between water (50 mL) and CH2Cl2 (100 mL)
  3. washThe organic phase was washed with sodium hydroxide (5%, aq.), water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-eb17e2879cbb458f92d7c828803f90e4
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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