Sodium Sulfate → 3-Pyridineethanol

HRID 414117Notes

Reaction equation

HRID 414117 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9](O)=[O:10])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][OH:10])[CH:3]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 21226445Aluminium lithium hydride

Product 1

HCID 805153-PyridineethanolYield 34.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A round-bottomed flask equipped with a magnetic stirring bar is charged with 13.9 g (0.08 mol) of (3-pyridinyl)acetic acid, hydrochloride salt (Aldrich Chemical Co.) and 400 ml of tetrahydrofuran (THF) under a nitrogen atmoshphere. To this solution lithium aluminum hydride (6.0 g, 0.16 mol) is added at room temperature for 24 hr. Saturated aqueous sodium sulfate is then added dropwise until the mixture becomes white. The solution is dried over anhydrous sodium sulfate. After filtration and concentration the resulting yellow oil is purified by 324 g of HPLC grade silica gel, eluting with ethyl acetate-hexane-ethanol (10:1:1) and collecting 40 ml fractions. Fractions 21-43 homogeneous on TLC are combined and concentrated in vacuo to give a light yellow oil (3.4 g, 34%).

Workup

  1. customA round-bottomed flask equipped with a magnetic stirring bar
  2. dry with materialThe solution is dried over anhydrous sodium sulfate
  3. filtrationAfter filtration and concentration the resulting yellow oil
  4. customis purified by 324 g of HPLC grade silica gel
  5. washeluting with ethyl acetate-hexane-ethanol (10:1:1)
  6. customcollecting 40 ml fractions
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd4d3671609c47b3b9e1a27e66c336f8
Source dataset
uspto-grants-1988_12
Patent number
US04789745

Reaction notes

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