Boron trifluoride etherate → (2-Chloropyridin-4-yl)methanol

HRID 1257101Notes

Reaction equation

HRID 1257101 reaction equation
B(F)(F)F.CCOCC.[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][N:19]=1)[C:14](O)=[O:15].[BH4-].[Na+]>C1COCC1>[Cl:10][C:11]1[CH:12]=[C:13]([CH2:14][OH:15])[CH:17]=[CH:18][N:19]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 2369852-Chloroisonicotinic acidHCID 4311764Sodium borohydride

Product 1

HCID 7062237(2-Chloropyridin-4-yl)methanolYield 85.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Boron trifluoride diethyl etherate (71 g, 0.5 mol) was added dropwise to a suspension of 2-chloroisonicotinic acid (20 g, 0.125 mol) and sodium borohydride (14.3 g, 0.376 mol) in THF (200 mL) with stirring at −10˜−5° C., then the mixture was stirred at room temperature overnight. The reaction mixture was quenched with water (100 mL), and extracted with ethyl acetate (3×200 mL). The organic layers were combined, washed with brine (200 mL), dried over anhydrous Na2SO4, filtered and concentrated to dryness. The crude material was further purified by silica gel chromatography (EtOAc/Hexane=1/4) and afforded 2-chloro-4-(hydroxymethyl)pyridine (15.4 g, 85.8% yield) as an oil.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe reaction mixture was quenched with water (100 mL)
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. washwashed with brine (200 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude material was further purified by silica gel chromatography (EtOAc/Hexane=1/4)

Sources & evidence

ORD record
ord-35a392f32b374022802267c7527bc19e
Source dataset
uspto-grants-2013_06
Patent number
US08461339B2

Reaction notes

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