Ethylene Oxide → γ-Methyl-4-pyridinepropanol

HRID 1154326Notes

Reaction equation

HRID 1154326 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH2:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)[CH3:10].[CH2:17]1[O:19][CH2:18]1>O>[N:14]1[CH:15]=[CH:16][C:11]([CH:9]([CH3:10])[CH2:18][CH2:17][OH:19])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 108224-EthylpyridineHCID 2724682Lithium diisopropylamide

Product 1

HCID 20434905γ-Methyl-4-pyridinepropanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of lithium diisopropylamide [made from n-BuLi (13.3 cm3) and diisopropylamine (2.8 cm3) in T.H.F. (10 cm3)] was added at -70° to a stirred solution of 4-ethylpyridine (2.0 g) in T.H.F. (10 cm3) under nitrogen. After 10 minutes the red solution was treated with ethylene oxide (1 cm3) giving an immediate suspension. After warming to room temperature, water (10 cm3) was added and the phases were separated. The aqueous phase was extracted with chloroform (2×20 cm3) and the combined organic extracts were dried (MgSO4) and evaporated in vacuo. Chromatography on silica (Merck 60.9385) eluting with methanol: ethyl acetate, 3:20, gave 3-(4-pyridyl)-butan-1-ol as an oil.

Workup

  1. customgiving an immediate suspension
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with chloroform (2×20 cm3)
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. customevaporated in vacuo
  6. washChromatography on silica (Merck 60.9385) eluting with methanol

Sources & evidence

ORD record
ord-ac0b299e3da541ada700506dd016f00a
Source dataset
uspto-grants-1984_12
Patent number
US04489075

Reaction notes

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