4-Chloropyridine-3-carbaldehyde → HCID 23436208, compound

HRID 2121267Notes

Reaction equation

HRID 2121267 reaction equation
[CH2:1]([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[CH:13]=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Cl:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[CH:13]=[CH2:1]

Participants

5

Reactant 2

HCID 140466744-Chloropyridine-3-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 23436208HCID 23436208, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyltriphenylphosphonium bromide (4.45 g, 12.5 mmol) was suspended in THF (25 mL) under dry nitrogen and treated with butyllithium (2.5 M in hexanes, 5 mL). After stirring the suspension for 30 minutes, 4-chloropyridine-3-carboxaldehyde (1.47 g, 10.4 mmol) was added. After 2 hours at ambient temperature, the reaction was diluted with hexanes, filtered, and evaporated. The material thus obtained was used directly without further purification or characterization.

Workup

  1. waitAfter 2 hours at ambient temperature
  2. filtrationfiltered
  3. customevaporated
  4. customThe material thus obtained
  5. customwas used directly without further purification or characterization

Sources & evidence

ORD record
ord-8261633573334b0aad9f1885157fad3c
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

Loading…