3-Pyridinecarboxaldehyde → 1-(Pyridin-3-yl)propan-1-ol

HRID 1186324Notes

Reaction equation

HRID 1186324 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=[O:12])[CH:6]=1>O1CCCC1>[OH:12][CH:11]([C:7]1[CH:6]=[N:5][CH:10]=[CH:9][CH:8]=1)[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 110839421-(Pyridin-3-yl)propan-1-olYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-1, by use of ethylmagnesium bromide (a 1.0 mol/L solution in tetrahydrofuran, 3.18 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-hydroxypropyl)pyridine (Compound CC) (194 mg, yield: 67%).

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-3086b0d93ab64f6583a340958d82633f
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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