Diisopropylamine → HCID 23503598, compound

HRID 1835422Notes

Reaction equation

HRID 1835422 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][C:17]([Cl:21])=[CH:16][N:15]=1.[CH3:22][O:23][C:24]1[C:31]([O:32][CH3:33])=[C:30]([O:34][CH3:35])[CH:29]=[C:28]([CH3:36])[C:25]=1[CH:26]=[O:27]>C1(C)C=CC=CC=1.C(OCC)C>[CH3:22][O:23][C:24]1[C:31]([O:32][CH3:33])=[C:30]([O:34][CH3:35])[CH:29]=[C:28]([CH3:36])[C:25]=1[CH:26]([C:18]1[C:17]([Cl:21])=[CH:16][N:15]=[C:14]([Cl:13])[C:19]=1[Cl:20])[OH:27]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 27666Pyridine, 2,3,5-trichloro-HCID 896832,3,4-Trimethoxy-6-methylbenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 23503598HCID 23503598, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

17.2 ml (26.7 mmol) of n-butyllithium (1.56 M hexane solution) was dropwise added to a diethyl ether (20 ml) solution of 2.7 g (26.7 mmol) of diisopropylamine at 0° C., followed by stirring for 1 hour. The solution was cooled to −78° C., a toluene solution of 4.8 g (26.7 mmol) of 2,3,5-trichloropyridine was dropwise added thereto, and then a toluene solution of 5.0 g (24.0 mmol) of 2,3,4-trimethoxy-6-methylbenzaldehyde was dropwise added thereto, followed by stirring for 30 minutes. The temperature was recovered to room temperature, and stirring was carried out further for 1 hour. 30 ml of water was added to the mixture to terminate the reaction, and ethyl acetate was added for extraction. The organic layer was dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 6.7 g (yield 72%) of amorphous (2,3,4-trimethoxy-6-methylphenyl)(2,3,5-trichloro-4-pyridyl)methanol.

Workup

  1. stirringby stirring for 30 minutes
  2. customThe temperature was recovered to room temperature
  3. stirringstirring
  4. waitwas carried out further for 1 hour
  5. addition30 ml of water was added to the mixture
  6. customto terminate
  7. customthe reaction, and ethyl acetate
  8. additionwas added for extraction
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. filtrationsubjected to filtration
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe crude product thus obtained
  13. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-89ccdaadf4ff4fce931e5a2d30dc9d9a
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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