Water → HCID 18552266, compound

HRID 1264459Notes

Reaction equation

HRID 1264459 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=2)[CH:5]=[C:4]([F:19])[CH:3]=1.[Li]CCCC.[CH:25](N1CCCCC1)=[O:26].O>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:12][CH:13]=2)[CH:5]=[C:4]([F:19])[C:3]=1[CH:25]=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 174291-PiperidinecarboxaldehydeHCID 185522753,5-Difluoro-4'-pentyl-1,1'-biphenylHCID 178418339Butyllithium

Product 1

HCID 18552266HCID 18552266, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 500-ml three-neck flask equipped with a stirrer, a thermometer and a dropping funnel, 15.0 g (57.6 mmol) of 2,6-difluoro-4-(4-pentylphenyl)benzene was dissolved in 100 ml of THF under nitrogen atmosphere, and 43 ml (69.1 mmol) of n-BuLi (1.6M cyclohexane solution) was added dropwise at −65° C. or lower while stirring, followed by further stirring for one hour. Then, 7.2 g (63.4 mmol) of formylpiperidine was added dropwise thereto at −65° C. or lower, and the solution was further stirred for 2 hours. 200 ml of water was added to the reaction mixture, which was extracted with 400 ml of toluene, and the toluene layer was washed twice with 200 ml of water and then dried over anhydrous magnesium sulfate. Toluene was distilled off under reduced pressure, and the residue was purified by means of a silica gel column chromatography with toluene as a developing solvent to obtain 13.1 g of 2,6-difluoro-4-(4-pentylphenyl)benzaldehyde.

Workup

  1. customIn a 500-ml three-neck flask equipped with a stirrer
  2. stirringby further stirring for one hour
  3. stirringat −65° C. or lower, and the solution was further stirred for 2 hours
  4. extractionwas extracted with 400 ml of toluene
  5. washthe toluene layer was washed twice with 200 ml of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationToluene was distilled off under reduced pressure
  8. customthe residue was purified by means of a silica gel column chromatography with toluene as a developing solvent

Sources & evidence

ORD record
ord-49f73ac5acd04640bb328ea0b7e655ba
Source dataset
uspto-grants-2003_04
Patent number
US06544604B2

Reaction notes

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