Ethanol → (2-Chloropyridin-3-yl)methanol

HRID 1405706Notes

Reaction equation

HRID 1405706 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].C1COCC1.C(O)C.[BH4-].[Na+]>O>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:8][CH:9]=[CH:10][N:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 819931Methyl 2-chloronicotinateHCID 4311764Sodium borohydride

Product 1

HCID 2763647(2-Chloropyridin-3-yl)methanolYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 2-chloronicotinate (5 g), dehydrated THF (30 mL) and ethanol (30 mL) was added sodium borohydride (4.41 g) at 0° C. The reaction mixture was stirred at room temperature overnight, poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.22 g) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-43449beff2c64308bc81f88cc5003c45
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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