Water → HCID 69292149, compound

HRID 900767Notes

Reaction equation

HRID 900767 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[F:10][C:11]1[C:16]([Li])=[CH:15][CH:14]=[CH:13][N:12]=1.O>C1COCC1.CCOCC.C(Cl)(Cl)Cl.O=[Mn]=O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([C:16]2[C:11]([F:10])=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:7])=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 962WaterHCID 680234-FluorobenzaldehydeHCID 178506731HCID 178506731, compound

Product 1

HCID 69292149HCID 69292149, compound

Reagents, catalysts & solvents 4

HCID 14801Manganese dioxideCatalystHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-fluorobenzaldehyde (5.86 g, 45 mmol) in dry THF (10 ml) was dropwise added at −70° C. to a solution of 2-fluoro-3-lithiopyridine (prepared from 2-fluoropyridine (3.91 ml, 45 mmol) and LDA (49.5 mmol)) in THF (120 ml). After complete addition, the cooling bath was removed and the reaction was allowed to reach 10° C. Hydrolysis was performed by addition of water, and the mixture is then diluted with ether. After separation of the layers, the ether solution was washed with brine, dried over Na2SO4 and evaporated in vacuum to yield a viscous oil. The alcohol was dissolved in CHCl3 (150 ml) and MnO2 (58.62 g, 0.675 mol) was added at room temperature. After 16 hours, the mixture was filtered on a pad of Celite and concentrated. The residual oil was chromatographied on silica gel (CH2Cl2) and (4-fluorophenyl)(2-fluoro-3-pyridinyl)methanone 37 was isolated as a white solid (4.83 g, 49%).

Workup

  1. additionAfter complete addition
  2. customthe cooling bath was removed
  3. customto reach 10° C
  4. customHydrolysis
  5. customAfter separation of the layers
  6. washthe ether solution was washed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated in vacuum
  9. customto yield a viscous oil
  10. filtrationthe mixture was filtered on a pad of Celite
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-1dca0de9682f4f719580b78a69dfed37
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

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