Water → 1-(4-Pyridyl)-3-buten-1-ol

HRID 1612629Notes

Reaction equation

HRID 1612629 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[CH2:9]([Li])[CH:10]=[CH2:11].O>C1COCC1>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([OH:8])[CH2:11][CH:10]=[CH2:9])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 133894-PyridinecarboxaldehydeHCID 178506856HCID 178506856, compound2×

Product 1

HCID 156829571-(4-Pyridyl)-3-buten-1-olYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4.75 g (50 mmol) of pyridine-4-carboxaldehyde was dissolved in 50 ml THF and cooled to 0° C. Allyl lithium was then added with stirring until the mixture turned the dark color characteristic of the allyl lithium solution. After stirring for an additional 5 minutes, water was slowly added at 0° C. until two phases formed and all precipitate was dissolved. The THF layer was separated, dried over MgSO4, and evaporated in vacuo to an oil. Flash chromatography yielded 4.69 g (63%) of product as an oil. 1H NMR (CDCL3): 8.5 and 7.3 (4H, pyridyl), 5.8 and 5.15 (3H, vinyl), 4.75 (1H, CHOH), 3.6 (1H, OH), and 2.5 (2H, CH2) ppm.

Workup

  1. stirringAfter stirring for an additional 5 minutes
  2. customformed
  3. dissolutionall precipitate was dissolved
  4. customThe THF layer was separated
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo to an oil

Sources & evidence

ORD record
ord-2a0c5c3625a84fdea69b1f574b21b5da
Source dataset
uspto-grants-1993_03
Patent number
US05190929

Reaction notes

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