Sodium Hydroxide → 4-Ethenylquinoline

HRID 1077409Notes

Reaction equation

HRID 1077409 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=O)=[CH:3][CH:2]=1.[I-].[C:14]1(C([PH3+])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>C1C=CC=CC=1>[CH:11]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1)=[CH2:14]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 780724-QuinolinecarboxaldehydeHCID 66599960Tritylphosphanium iodide

Product 1

HCID 133195774-Ethenylquinoline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 4-quinolinecarboxaldehyde (5 g; 3.18×10-2 mol) in 32 ml of benzene, containing triphenylmethylphosphonium iodide (26 g; 6.36×10-2 mol), is added under an inert atmosphere to sodium hydroxide solution (96 ml; 5N). The two-phase system is stirred at 45° C. for 30 minutes. After allowing the phases to separate by settling, the aqueous phase is extracted with ethyl acetate (3×100 ml). The organic phases are combined and washed with 1N HCl solution (2×30 ml), then the aqueous phase is neutralized with NaHCO3 and extracted with methylene chloride (3×100 ml). The organic phase is dried over MgSO4. The desired product is purified by chromatography on a MERCK F254 silica column (eluent=cyclohexane/AcOEt, 8:2). Yield=2.8 g (60%).

Workup

  1. customto separate
  2. extractionthe aqueous phase is extracted with ethyl acetate (3×100 ml)
  3. washwashed with 1N HCl solution (2×30 ml)
  4. extractionextracted with methylene chloride (3×100 ml)
  5. dry with materialThe organic phase is dried over MgSO4
  6. customThe desired product is purified by chromatography on a MERCK F254 silica column (eluent=cyclohexane/AcOEt, 8:2)

Sources & evidence

ORD record
ord-35fcb7d45b2046798ae52896d37a719d
Source dataset
uspto-grants-1996_08
Patent number
US05543298

Reaction notes

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