Ethyl 3-pyridylacetate → 3-Pyridineethanol

HRID 536171Notes

Reaction equation

HRID 536171 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)C.[BH4-].[Na+]>CO>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH2:5][CH2:4][OH:3])[CH:7]=1

Participants

4

Reactant 2

HCID 96490Ethyl 3-pyridylacetateHCID 4311764Sodium borohydride

Product 1

HCID 805153-PyridineethanolYield 85.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of pyridin-3-yl-acetic acid ethyl ester (33 g, 197.36 mmol) in methanol (400 mL) was added sodium borohydride (74.66 g, 1.9 mole). The reaction mixture was refluxed for 12 h, then cooled to rt, quenched with water (300 mL), concentrated. The residue was extracted with DCM (500 mL), dried over sodium sulfate, concentrated to afford the title product (20.76 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 12 h
  2. customquenched with water (300 mL)
  3. concentrationconcentrated
  4. extractionThe residue was extracted with DCM (500 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8edcb35f503d44abac9870451cc76649
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

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