2-Fluoro-5-formylpyridine → 1-(6-Fluoropyridin-3-yl)ethan-1-ol

HRID 1640873Notes

Reaction equation

HRID 1640873 reaction equation
[CH3:1][Mg]Br.[F:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][CH:6]=1>C1COCC1>[F:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]([OH:12])[CH3:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 164142462-Fluoro-5-formylpyridineHCID 178418573HCID 178418573, compound

Product 1

HCID 666001661-(6-Fluoropyridin-3-yl)ethan-1-olYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add methylmagnesium bromide (3 M in ether, 12 mL, 36 mmol) at 0° C. under nitrogen to a solution of 6-fluoro-pyridine-3-carbaldehyde (3 g, 24 mmol) in THF (20 mL). Continue to stir the mixture overnight at RT. Quench the mixture with 1 N HCl, followed by basification with diluted ammonium hydroxide to ˜pH 9. Extract the product with chloroform/IPA (3/1). Dry over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (10% methanol in DCM) to give the title compound as a colorless oil (2.3 g, 68%). MS (ES) m/z 142 [M+1]+.

Workup

  1. customQuench the mixture with 1 N HCl
  2. extractionExtract the product with chloroform/IPA (3/1)
  3. dry with materialDry over sodium sulfate
  4. concentrationConcentrate the solution in vacuo
  5. customPurify by column chromatography (10% methanol in DCM)

Sources & evidence

ORD record
ord-ee6091d87c37483282af25544349b5c6
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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