Tetrahydrofuran → Methanone, (6-chloro-3-pyridinyl)(4-methoxyphenyl)-

HRID 626154Notes

Reaction equation

HRID 626154 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([Mg]Br)=[CH:14][CH:13]=1.[NH4+].[Cl-].C1C[O:25]CC1>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)=[O:25])=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 178491912HCID 178491912, compound

Product 1

HCID 11413955Methanone, (6-chloro-3-pyridinyl)(4-methoxyphenyl)-Yield 50%

Conditions

Temperature
0 °C

Procedure

To a solution of 6-chloronicotinonitrile (1.39 g, 10 mmol) in 100 mL of THF was added (4-methoxyphenyl)magnesium bromide (15 mmol) dropwise at 0° C. The mixture was then stirred at 0° C. for 1 h. and then 50 mL sat. NH4Cl solution was added. The mixture was extracted with ethyl acetate and the organic layer was washed with brine, dried over Na2SO4, filtered, concentrated, and purified by flash chromatography to give the product (1.24 g, 50% yield).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-89a73a1d11304a0abfb73d64c4681dfb
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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