Sodium Hydroxide → 4-Pyridineethanol

HRID 586353Notes

Reaction equation

HRID 586353 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8](OCC)=[O:9])=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C(OCC)C>[OH:9][CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 736321Ethyl pyridine-4-acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 729214-PyridineethanolYield 54.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 4-pyridylacetate (20 g, 121 mmol) was added to a suspension of LiAlH4 (9.2 g, 242 mmol) in diethyl ether (600 mL). Diatomaceous earth (about 50 mL) was added to aid stirring. The mixture stirred overnight. The mixture was cooled to 0° C. and aqueous NaOH (15%) was added until degassing ceased. The mixture was allowed to stir for 1 h. The solids were removed by filtration and the filtrate was concentrated under vacuum. The crude product was purified by chromatography (SiO2, 40:1-20:1 CH2Cl2:methanol) to provide 4-(2-hydroxyethyl)pyridine (8.1 g, 54%) as an amber liquid.

Workup

  1. additionDiatomaceous earth (about 50 mL) was added to aid
  2. stirringThe mixture stirred overnight
  3. customuntil degassing
  4. stirringto stir for 1 h
  5. customThe solids were removed by filtration
  6. concentrationthe filtrate was concentrated under vacuum
  7. customThe crude product was purified by chromatography (SiO2, 40:1-20:1 CH2Cl2:methanol)

Sources & evidence

ORD record
ord-a32fbd2eb18242fc92928ba424dceaef
Source dataset
uspto-grants-2005_08
Patent number
US06936611B2

Reaction notes

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