Thionyl Chloride → (2-Chloro-4-phenylpyridin-3-yl)methanol

HRID 1863990Notes

Reaction equation

HRID 1863990 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[C:4](O)=[O:5].S(Cl)(Cl)=O>O1CCCC1>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[C:7]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 183873122-Chloro-4-phenylnicotinic acid

Product 1

HCID 23089956(2-Chloro-4-phenylpyridin-3-yl)methanolYield 71.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-4-phenylnicotinic acid (22.4 g) in tetrahydrofuran (200 ml) was added thionyl chloride (21 ml), and the mixture was heated under reflux for 3 hrs. The solvent was evaporated under reduced pressure, and the precipitated solid was collected by filtration and washed with hexane. The obtained powdery solid was dissolved in tetrahydrofuran (200 ml), and lithium aluminum hydride (4.5 g) was added by small portions while cooling in a dry ice-acetone bath. The mixture was stirred under cooling for 5 min. and water was added to quench the reaction. The precipitated solid was filtered off, and the filtrate was concentrated and extracted with ethyl acetate. The organic layer was washed successively with water, saturated aqueous sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (15.1 g) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with hexane
  6. dissolutionThe obtained powdery solid was dissolved in tetrahydrofuran (200 ml)
  7. additionlithium aluminum hydride (4.5 g) was added by small portions
  8. temperaturewhile cooling in a dry ice-acetone bath
  9. temperatureunder cooling for 5 min.
  10. additionwater was added
  11. customto quench
  12. customthe reaction
  13. filtrationThe precipitated solid was filtered off
  14. concentrationthe filtrate was concentrated
  15. extractionextracted with ethyl acetate
  16. washThe organic layer was washed successively with water, saturated aqueous sodium hydrogencarbonate and saturated brine
  17. dry with materialdried over anhydrous magnesium sulfate
  18. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ed4f0f1c03ee40ba92bc4b4b945ae41f
Source dataset
uspto-grants-2009_12
Patent number
US07625887B2

Reaction notes

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