6-Methyl-2-pyridinecarboxaldehyde → 1-(6-Methylpyridin-2-yl)ethanol

HRID 917673

Reaction equation

HRID 917673 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:10][Mg]Br>O1CCCC1>[CH3:1][C:2]1[N:7]=[C:6]([CH:8]([OH:9])[CH3:10])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 3531381-(6-Methylpyridin-2-yl)ethanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a −60° C. solution of 6-methyl-pyridine-2-carbaldehyde (25 g, 206 mmol) in tetrahydrofuran (200 mL) was added methyl magnesium bromide (200 mL, 1.4 M in tetrahydrofuran/toluene, 1.36 equiv) over 40 minutes. The reaction mixture was slowly warmed to −10° C. over 90 minutes, and then slowly quenched with saturated aqueous ammonium chloride (75 mL). The liquid phase was decanted from the solids and concentrated in vacuo. The resulting residue was dissolved in methylene chloride, dried over magnesium sulfate, and concentrated in vacuo to yield 1-(6-Methyl-pyridin-2-yl)-ethanol (28 g, 100%).

Workup

  1. customslowly quenched with saturated aqueous ammonium chloride (75 mL)
  2. customThe liquid phase was decanted from the solids
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting residue was dissolved in methylene chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f46f5dc404e4471ac09b56fdf5b8021
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Linked notes

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