6-Chloropyridine-3-carbaldehyde → HCID 117778379, compound

HRID 1503244Notes

Reaction equation

HRID 1503244 reaction equation
[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)C=CC=CC=1.[Cl:32][C:33]1[N:38]=[CH:37][C:36]([CH:39]=O)=[CH:35][CH:34]=1.CC(C)([O-])C.[Na+]>C(O)C>[Cl:32][C:33]1[CH:34]=[CH:35][C:36](/[CH:39]=[CH:9]/[C:10]2[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=2)=[CH:37][N:38]=1

Participants

5

Reactant 3

HCID 27640536-Chloropyridine-3-carbaldehydeHCID 10391293Phosphonium, triphenyl[[4-(trifluoromethyl)phenyl]methyl]-, bromideHCID 23676156Sodium t-butoxide

Product 1

HCID 117778379HCID 117778379, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triphenyl[4-(trifluoromethyl)benzyl]phosphonium bromide (6.4 g) and 6-chloropyridine-3-carboxaldehyde (1.8 g) were dissolved in ethanol (120 mL). To the solution, sodium tert-butoxide (1.2 g) was added at room temperature, and the mixture was stirred for 1 hour. The solvent was distilled off under reduced pressure, and ethyl acetate was added to the residue. The organic layer was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (Yamazen Corporation, elution solvent: hexane/ethyl acetate). The obtained solid was washed with hexane to obtain the title compound (0.89 g) (yield: 25%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and ethyl acetate
  2. additionwas added to the residue
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (Yamazen Corporation, elution solvent: hexane/ethyl acetate)
  7. washThe obtained solid was washed with hexane

Sources & evidence

ORD record
ord-00bab5032f7e4777b4b330a604dd6db0
Source dataset
uspto-grants-2015_12
Patent number
US09212170B2

Reaction notes

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