Water → 1-(5-Fluoropyridin-2-yl)ethan-1-ol

HRID 1694537Notes

Reaction equation

HRID 1694537 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[CH3:10][Li].[Cl-].[NH4+].O>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:9])[CH3:10])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 103516975-Fluoropyridine-2-carboxaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 591868831-(5-Fluoropyridin-2-yl)ethan-1-olYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −78° C. solution of 5-fluoro-2-formylpyridine (0.66 g, 5.3 mmol) in THF (20 mL) was methyl lithium (1.6 M in diethyl ether, 4.0 mL) added dropwise. After stirring for 1.5 h at −78° C. a saturated solution of ammonium chloride (25 mL) followed by water (25 mL) was added. The mixture was extracted with chloroform and the organic phase was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by flash column chromatography (eluent: chloroform:methanol 98:2) affording the title compound (0.25 g, 33% yield).

Workup

  1. customTo a −78° C.
  2. additionadded dropwise
  3. additionwas added
  4. extractionThe mixture was extracted with chloroform
  5. dry with materialthe organic phase was dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (eluent: chloroform:methanol 98:2)

Sources & evidence

ORD record
ord-028b7fce95514d5783aa772c4a69bb85
Source dataset
uspto-grants-2012_04
Patent number
US08158785B2

Reaction notes

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