(2-Methylbenzyl)triphenylphosphonium bromide → HCID 22678406, compound

HRID 1837764

Reaction equation

HRID 1837764 reaction equation
[Br-].[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH3:35][O:36][C:37]1[C:42]([CH2:43][N:44]2[CH2:49][CH2:48][CH:47]([CH:50]=O)[CH2:46][CH2:45]2)=[CH:41][CH:40]=[CH:39][N:38]=1>CN(C)C=O>[CH3:35][O:36][C:37]1[C:42]([CH2:43][N:44]2[CH2:49][CH2:48][CH:47](/[CH:50]=[CH:9]/[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[CH3:2])[CH2:46][CH2:45]2)=[CH:41][CH:40]=[CH:39][N:38]=1

Participants

5

Reactant 3

HCID 197738(2-Methylbenzyl)triphenylphosphonium bromideHCID 22678407HCID 22678407, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22678406HCID 22678406, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In N,N-dimethylformamide (10 ml) was suspended 1.15 g of [(2-methylphenyl)methyl]triphenylphosphonium bromide. To the suspension was added 288 mg of potassium tert-butoxide, followed by stirring for 15 minutes under ice-cooling. A solution of 500 mg of 1-[(2-methoxy-3-pyridinyl)methyl]-4-piperidinecarboxaldehyde dissolved in 3 ml of N,N-dimethylformamide was added dropwise thereinto, followed by stirring at room temperature overnight. Ice-water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1), to give 473 mg of the title compound as a pale yellow oil.

Workup

  1. temperaturecooling
  2. additionwas added dropwise
  3. stirringby stirring at room temperature overnight
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5008ffafba3d4d41b0877944cafd41a9
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Linked notes

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