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

HRID 1892432Notes

Reaction equation

HRID 1892432 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-8a78545c110046d4aafe6e3d6b922007
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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