Water → 2-(Pyridin-3-yloxy)ethan-1-ol

HRID 2108127Notes

Reaction equation

HRID 2108127 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][C:9](OC)=[O:10])[CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][OH:10])[CH:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23008475Methyl 2-(pyridin-3-yloxy)acetate

Product 1

HCID 219089972-(Pyridin-3-yloxy)ethan-1-olYield 86.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Methyl [(3-pyridinyl)oxy]acetate (3.6 g) in diethyl ether (80 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (826 mg) in diethyl ether (100 ml) at 0°. The mixture was stirred overnight at room temperature under nitrogen, water (1 ml) was added, followed by 2N sodium hydroxide (1 ml) and water (3 ml). The suspension was filtered and washed with ethyl acetate (3×100 ml) then dichloromethane (300 ml). The combined organic extracts were dried and concentrated to give the title compound (2.6 g) as an oil. T.l.c. (System E 80:20:1) Rf 0.31

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with ethyl acetate (3×100 ml)
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1b66040e64ed4aba80be8df54d3b06fd
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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