3-Pyridinecarboxaldehyde → 2-Methyl-1-(pyridin-3-yl)propan-1-ol

HRID 1186326Notes

Reaction equation

HRID 1186326 reaction equation
[CH:1]([Mg]Br)([CH3:3])[CH3:2].[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]=[O:13])[CH:7]=1>O1CCCC1>[OH:13][CH:12]([C:8]1[CH:7]=[N:6][CH:11]=[CH:10][CH:9]=1)[CH:1]([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 178418365HCID 178418365, compound

Product 1

HCID 135614132-Methyl-1-(pyridin-3-yl)propan-1-olYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-1, by use of isopropylmagnesium bromide (a 0.76 mol/L solution in tetrahydrofuran, 4.18 mL, 3.18 mmol), 3-pyridinecarboxaldehyde (200 μL, 2.12 mmol) and tetrahydrofuran (2.0 mL), the mixture was stirred and reacted at 0° C. for 1 hour. Then, purification by silica gel column chromatography (chloroform/methanol=9/1) was performed to give 3-(1-hydroxy-2-methylpropyl)pyridine (Compound CE) (69.0 mg, yield: 22%).

Workup

  1. customreacted at 0° C. for 1 hour
  2. customThen, purification by silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-0f1c3194e8924637b152d430ba84cae5
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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