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

HRID 1747907Notes

Reaction equation

HRID 1747907 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-72ddbbd297994e30bd5f586f1370174a
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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