Hydrochloric Acid → 1-(6-Fluoropyridin-3-yl)ethan-1-ol

HRID 561006

Reaction equation

HRID 561006 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.Cl.[OH-].[NH4+]>C1COCC1.C(Cl)(Cl)Cl.C(O)(C)C>[F:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]([OH:12])[CH3:1])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 164142462-Fluoro-5-formylpyridineHCID 178418573HCID 178418573, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

Add methyl magnesium 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 for overnight at room temperature. Hydrolyze the mixture with 1 N HCl and follow the basification with diluted ammonium hydroxide to ˜pH 9. Abstract the product with chloroform/isopropyl alcohol (3/1). Dry over sodium sulfate. Concentrate the solution in vacuo to yellow oil. Purify by column chromatography (10% methanol in dichloromethane) to give the product as a colorless oil (2.3 g, 68%). MS (ES) m/z 142 [M+1]+.

Workup

  1. dry with materialDry over sodium sulfate
  2. concentrationConcentrate the solution in vacuo to yellow oil
  3. customPurify by column chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9320ac8ebfc5459a8789f9592ea7f261
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Linked notes

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