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

HRID 339660Notes

Reaction equation

HRID 339660 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, 35.678 mmol) was slowly added under an atmosphere of dry N2 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 and then concentrated under reduced pressure. The resulting oil was diluted with water (200 mL) and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure to give 5.36 g (88%) of 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 EtOAc
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e0ef89dcf3d42ca972eee89002955a8
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

Loading…