Tetrahydrofuran → (6-Chloro-pyridin-2-yl)-ethanol

HRID 1910743Notes

Reaction equation

HRID 1910743 reaction equation
C(O[C:4](=O)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[N:7]=1)C.[O:14]1CCCC1>>[Cl:12][C:8]1[N:7]=[C:6]([CH:5]([OH:14])[CH3:4])[CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 18928624Ethyl 2-(6-chloropyridin-2-yl)acetate

Product 1

HCID 20094872(6-Chloro-pyridin-2-yl)-ethanolYield 54%

Procedure

A solution of (6-chloro-pyridin-2-yl)-acetic acid ethyl ester (1.8 g, 9.05 mmol) in dry tetrahydrofuran (25 mL) was cooled to 0° C. Borane-dimethylsulfide complex (4.35 mL, 45.25 mmol) was added dropwise and the reaction mixture warmed to room temperature before heating at reflux overnight. The mixture was cooled to room temperature and quenched into saturated ammonium chloride solution and extracted with ethyl acetate. The separated organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product which was purified by column chromatography over silica gel (60-120 mesh) using 30% ethyl acetate in chloroform as eluent to afford (6-chloro-pyridin-2-yl)-ethanol (0.76 g, 54%) as a liquid.

Workup

  1. additionBorane-dimethylsulfide complex (4.35 mL, 45.25 mmol) was added dropwise
  2. temperaturebefore heating
  3. temperatureat reflux overnight
  4. temperatureThe mixture was cooled to room temperature
  5. customquenched into saturated ammonium chloride solution
  6. extractionextracted with ethyl acetate
  7. washThe separated organic layer was washed with water, brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give the crude product which
  12. customwas purified by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-c6c09f0945c447abb225b8b6a7947a77
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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