2-(Benzyloxy) ethanol → 4-(2-Benzyloxy-ethoxy)-2-chloro-pyridine

HRID 1910749Notes

Reaction equation

HRID 1910749 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:14][C:15]1[CH:20]=[C:19]([N+]([O-])=O)[CH:18]=[CH:17][N:16]=1>C1COCC1>[CH2:3]([O:10][CH2:11][CH2:12][O:13][C:19]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:14])[CH:20]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 121412-(Benzyloxy) ethanolHCID 24758Sodium hydrideHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 866395854-(2-Benzyloxy-ethoxy)-2-chloro-pyridineYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (50% in mineral oil; 0.54 g, 11.35 mmol) was added portionwise to a solution of 2-benzyloxylethanol (1.72 g, 11.4 mmol) in THF (15 mL) at r.t. under nitrogen. After 15 min. 2-chloro-4-nitro-pyridine (1.20 g, 7.57 mmol) was added and the reaction mixture stirred at r.t. overnight. The reaction mixture was quenched by slowly pouring onto ice and concentrated to remove the organic solvent. The residue was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine then dried over sodium sulfate, filtered and concentrated. The crude material was subjected to column chromatography over silica gel (60-120 mesh) using 5%-25% ethyl acetate in petroleum ether as eluent to afford 4-(2-benzyloxy-ethoxy)-2-chloro-pyridine (1.91 g, 96%) as an oily liquid.

Workup

  1. customThe reaction mixture was quenched
  2. additionby slowly pouring onto ice
  3. concentrationconcentrated
  4. customto remove the organic solvent
  5. additionThe residue was diluted with water
  6. extractionextracted with ethyl acetate
  7. washThe organic phase was washed with water and brine
  8. dry with materialthen dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-648163c129264566845842c6519675e5
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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