5,7-Difluoroquinoline-6-carbaldehyde → 1-(5,7-Difluoroquinolin-6-yl)ethanol

HRID 1959766Notes

Reaction equation

HRID 1959766 reaction equation
[F:1][C:2]1[C:11]([CH:12]=[O:13])=[C:10]([F:14])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH2:15]([Mg]I)C>C1COCC1>[F:1][C:2]1[C:11]([CH:12]([OH:13])[CH3:15])=[C:10]([F:14])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 579172825,7-Difluoroquinoline-6-carbaldehydeHCID 178461634HCID 178461634, compound

Product 1

HCID 581905601-(5,7-Difluoroquinolin-6-yl)ethanolYield 60.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5,7-difluoroquinoline-6-carbaldehyde (5.0 g, 25.9 mmol) in THF (80 mL) was added ethylmagnesium iodide (3 M, 9.5 mL, 28.5 mmol) at −78° C. After stirring at −78° C. for 1 hour, the reaction was quenched with saturated NH4Cl and concentrated under reduced pressure. The residue was diluted with water, extracted with DCM three times. The organic layers were combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by chromatography (hexane/EtOAc) to give the title compound as a white solid (3.3 g, 58%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.97 (dd, 1H), 8.47 (d, 1H), 7.66-7.58 (m, 2H), 5.54 (d, 1H), 5.29 (m, 1H), 1.56 (d, 3H). LCMS (method A): [MH]+=210, tR=4.71 min.

Workup

  1. customthe reaction was quenched with saturated NH4Cl
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with DCM three times
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-13401217761548d4b50b748a1a509761
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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