Ammonium Chloride → α,3-Dimethyl-4-pyridinemethanol

HRID 2092046Notes

Reaction equation

HRID 2092046 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[O:9].[CH3:10][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]([OH:9])[CH3:10]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 15018803-Methyl-4-pyridinecarboxaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 59574200α,3-Dimethyl-4-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methylpyridine-4-carbaldehyde (310.6 mg, 1.00 mmol) in tetrahydrofuran (6 mL) was mixed with methylmagnesium bromide (0.98 M in tetrahydrofuran, 4.74 mL, 4.65 mmol) under −78° C., and the mixture was warmed slowly to room temperature for 16 hours with stirring. After completion of the reaction, the reaction solution was mixed with saturated aqueous ammonium chloride and extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting crude reaction product containing the desired product was used for the next step (310.6 mg).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting crude reaction product

Sources & evidence

ORD record
ord-7bd446a8fcfb47f48736ffce306ac101
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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