2-Methoxyethanol → 2-Chloro-4-(2-methoxyethoxy)pyridine

HRID 876399Notes

Reaction equation

HRID 876399 reaction equation
CC([O-])(C)C.[K+].[Cl:7][C:8]1[CH:13]=[C:12]([N+]([O-])=O)[CH:11]=[CH:10][N:9]=1.[CH3:17][O:18][CH2:19][CH2:20][OH:21]>>[Cl:7][C:8]1[CH:13]=[C:12]([O:21][CH2:20][CH2:19][O:18][CH3:17])[CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 7351522-Chloro-4-nitropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 637775772-Chloro-4-(2-methoxyethoxy)pyridineYield 88.1%

Procedure

Potassium 2-methylpropan-2-olate (4.214 g, 35.68 mmol) was slowly added to a solution of 2-chloro-4-nitropyridine (5.142 g, 32.434 mmol) in 2-methoxyethanol (40.0 mL, 506.74 mmol). The reaction was stirred at ambient temperature for 2 hours, then concentrated under reduced pressure. The resulting oil was diluted with water (200 mL) and extracted with Ethyl acetate (2×100 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure to give 5.36 g (88%) of the desired product as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe resulting oil was diluted with water (200 mL)
  3. extractionextracted with Ethyl acetate (2×100 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d14de09b59d94cdf8d38aa7cbd599e6f
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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