Borane → (2-Chloropyridin-4-yl)methanol

HRID 2410258Notes

Reaction equation

HRID 2410258 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5](O)=[O:6].B>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 7062237(2-Chloropyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

2-Chloroisonicotinic acid (2.0 g; 12.7 mmol) is dissolved in 25 mL THF under anhydrous conditions and borane (1.0 M in THF; 25.4 ml; 25.4 mmol) is added drop wise via a syringe. The solution is stirred overnight at 50° C. The mixture is cooled to RT and quenched with 5 mL MeOH, concentrated under reduced pressure and purified by column chromatography on silica gel using a solvent gradient of hexanes to EtOAc. The final product is isolated as a white powder (1.1 g, 60% yield).

Workup

  1. additionis added drop wise via a syringe
  2. temperatureThe mixture is cooled to RT
  3. customquenched with 5 mL MeOH
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography on silica gel using a solvent gradient of hexanes to EtOAc

Sources & evidence

ORD record
ord-2a75bda1554c473fb5c7829c7d531fc4
Source dataset
uspto-grants-2014_08
Patent number
US08816082B2

Reaction notes

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