Sodium borohydride → 2-Chloro-alpha-methyl-4-pyridinemethanol

HRID 1399981Notes

Reaction equation

HRID 1399981 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131452551-(2-Chloropyridin-4-yl)ethan-1-one

Product 1

HCID 140536542-Chloro-alpha-methyl-4-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cold solution of 1-(2-chloro-4-pyridyl)ethanone (1.0 g, 6.42 mmol) in MeOH was added NaBH4 (0.73 g, 19.21 mmol) and the solution stirred at RT for 30 min. The reaction was then quenched with saturated NH4Cl solution followed by extraction with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried (Na2SO4) and evaporated in vacuo to obtain i (0.61 g, 60%). MS 158.10 [M+H]+.

Workup

  1. customThe reaction was then quenched with saturated NH4Cl solution
  2. extractionfollowed by extraction with EtOAc (3×100 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customto obtain i (0.61 g, 60%)

Sources & evidence

ORD record
ord-070f08d136924e75a1c395e6ca9d3bc1
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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