Sodium hydride → 3-[2-(4-Chloro-3-nitrophenyl)vinyl]pyridine

HRID 2099850Notes

Reaction equation

HRID 2099850 reaction equation
[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)C=CC=CC=1.[H-].[Na+].[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][C:32]=1[N+:39]([O-:41])=[O:40]>CN(C=O)C>[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=[CH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:33][C:32]=1[N+:39]([O-:41])=[O:40]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 855054-Chloro-3-nitrobenzaldehydeHCID 22325077Triphenyl(3-pyridylmethyl)phosphonium chloride

Product 1

HCID 690036093-[2-(4-Chloro-3-nitrophenyl)vinyl]pyridineYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triphenylpyridin-3-ylmethylphosphonium chloride (1.95 g) was added into an ice-cooled DMF suspension (40 ml) containing sodium hydride (60% in oil) (0.26 g), followed by 30 minutes of stirring at room temperature. The reaction solution was cooled to 0° C. and 4-chloro-3-nitrobenzaldehyde (1.04 g) was added portionwise thereto, followed by 2 hours of stirring at room temperature. To the residue formed by evaporating the reaction solution under reduced pressure was poured an appropriate amount of purified water, followed by extraction with ethyl acetate. Thereafter, the organic layer was dried over anhydrous magnesium sulfate. The crude product obtained by solvent evaporation was purified by silica gel column chromatography to obtain 3-[2-(4-chloro-3-nitrophenyl)vinyl]pyridine (0.86 g) from the fractions eluted with ethyl acetate-hexane (2:1 (v/v)).

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. waitfollowed by 2 hours
  3. stirringof stirring at room temperature
  4. customTo the residue formed
  5. customby evaporating the reaction solution under reduced pressure
  6. additionwas poured an appropriate amount of purified water
  7. extractionfollowed by extraction with ethyl acetate
  8. dry with materialThereafter, the organic layer was dried over anhydrous magnesium sulfate
  9. customThe crude product obtained by solvent evaporation
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0e41f3acf1fa488aa66625fdae717a2a
Source dataset
uspto-grants-2009_08
Patent number
US07569688B2

Reaction notes

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