Water → alpha-Methyl-3-pyridinemethanol

HRID 1790381Notes

Reaction equation

HRID 1790381 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8](OCC)=O)[CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH2:19]>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([OH:19])[CH3:8])[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 96490Ethyl 3-pyridylacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 101192alpha-Methyl-3-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-pyridylacetate (2.0 ml) was dissolved in tetrahydrofuran (66 ml). Under ice cooling, lithium aluminum hydride (0.5 g) was added thereto followed by stirring for 30 min. After adding water (0.5 ml), a 5 N aqueous solution of sodium hydroxide (0.5 ml) and further water (1.5 ml), the resulting precipitate was filtered off and washed with ethyl acetate. The filtrate was concentrated under reduced pressure to give the title compound (1.636 g) as a pale yellow oil (1.636 g) (yield: quantitative).

Workup

  1. filtrationa 5 N aqueous solution of sodium hydroxide (0.5 ml) and further water (1.5 ml), the resulting precipitate was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9c715bb37e9649afb3d25881488e8d52
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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