Water → 2-Ethoxy-4-iodo-3,5-dimethylpyridine

HRID 1043926Notes

Reaction equation

HRID 1043926 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].F[C:6]1[C:11]([CH3:12])=[C:10]([I:13])[C:9]([CH3:14])=[CH:8][N:7]=1.CC(OC)(C)C.O>C(O)C.C1COCC1>[CH2:2]([O:1][C:6]1[C:11]([CH3:12])=[C:10]([I:13])[C:9]([CH3:14])=[CH:8][N:7]=1)[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 15413tert-Butyl methyl etherHCID 2723922Sodium ethoxideHCID 735548982-Fluoro-4-iodo-3,5-dimethylpyridine

Product 1

HCID 866863502-Ethoxy-4-iodo-3,5-dimethylpyridine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 20% solution of sodium ethoxide in ethanol (123 mL) was added to a solution of 2-fluoro-4-iodo-3,5-dimethylpyridine obtained in Preparation Example 29(2) (400 mg) in THF (5 mL), and the mixed solution was stirred at room temperature overnight. The reaction mixture was cooled at 0° C., and MTBE (20 mL) and water (20 mL) were then added. The organic layer was separated. The organic layer was washed with brine. The combined aqueous layers were extracted with MTBE. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the title compound (423.8 mg).

Workup

  1. temperatureThe reaction mixture was cooled at 0° C.
  2. customThe organic layer was separated
  3. washThe organic layer was washed with brine
  4. extractionThe combined aqueous layers were extracted with MTBE
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-670cee03402942f08d5cfc92d6af8fae
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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