Hydride → 1-(4-Nitrophenyl)-3-pyridin-4-ylpropan-1-one

HRID 227605Notes

Reaction equation

HRID 227605 reaction equation
[H-].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:20])/[CH:12]=[CH:13]/[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)([O-:4])=[O:3]>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:20])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)([O-:4])=[O:3]

Participants

5

Reactant 2

HCID 166653HydrideHCID 6088197(2E)-1-(4-nitrophenyl)-3-pyridin-4-ylprop-2-en-1-one

Product 1

HCID 115940631-(4-Nitrophenyl)-3-pyridin-4-ylpropan-1-oneYield 113.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Trinbutyltin hydride (0.36 mL, 1.34 mmol) was added slowly by syringe pump to a room temperature mixture of Example 14A (0.2 g, 0.78 mmol) and Pd(PPh3)4 (27 mg, 0.023 mmol), stirred overnight, diluted with water, and extracted three times with ethyl acetate. The combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The concentrate was putrified by flash column chromatography on silica gel with 80% ethyl acetate/hexanes to provide 227 mg (100%) of the desired product. MS(ESI(−)) m/e 255 (M−H)−.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f86ec0830ef048e695ae8979b5f14c20
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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