Acetaldehyde → HCID 23503591, compound

HRID 1835413Notes

Reaction equation

HRID 1835413 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][O:14][C:15]1[C:20]([O:21][CH3:22])=[C:19]([O:23][CH3:24])[CH:18]=[C:17]([CH3:25])[C:16]=1[CH:26]([C:28]1[C:29]([Cl:39])=[N:30][C:31]([Cl:38])=[CH:32][C:33]=1[C:34]([F:37])([F:36])[F:35])[OH:27].[CH:40](=[O:42])[CH3:41]>O.O1CCCC1>[CH3:13][O:14][C:15]1[C:20]([O:21][CH3:22])=[C:19]([O:23][CH3:24])[CH:18]=[C:17]([CH3:25])[C:16]=1[CH:26]([C:28]1[C:29]([Cl:39])=[N:30][C:31]([Cl:38])=[C:32]([CH:40]([OH:42])[CH3:41])[C:33]=1[C:34]([F:35])([F:37])[F:36])[OH:27]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 7912DiisopropylamineHCID 12151532(2,3,4-Trimethoxy-6-methylphenyl)(2,6-dichloro-4-trifluoromethyl-3-pyridyl)methanolHCID 178418339Butyllithium

Product 1

HCID 23503591HCID 23503591, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

9.6 ml (14 mmol) of n-butyllithium (1.5 M hexane solution) was dropwise added to a tetrahydrofuran (16 ml) solution of 2.0 ml (14 mmol) of diisopropylamine at 0° C., followed by stirring for 30 minutes. The solution was cooled to −50° C., a tetrahydrofuran (11 ml) solution of 2.9 g (7 mmol) of (2,3,4-trimethoxy-6-methylphenyl)(2,6-dichloro-4-trifluoromethyl-3-pyridyl)methanol was added thereto, followed by stirring for 30 minutes, then the solution was cooled to −78° C., and acetaldehyde in an excess amount was added thereto, followed by stirring for 2 hours. 30 ml of water was added to the mixture to terminate the reaction, and tetrahydrofuran was distilled off under reduced pressure. Extraction with ethyl acetate was carried out, 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 2.5 g (yield 78%) of (2,3,4-trimethoxy-6-methylphenyl)(2,6-dichloro-5-(1-hydroxyethyl)-4-trifluoromethyl-3-pyridyl)methanol.

Workup

  1. stirringby stirring for 30 minutes
  2. temperaturethe solution was cooled to −78° C.
  3. stirringby stirring for 2 hours
  4. customto terminate
  5. customthe reaction, and tetrahydrofuran
  6. distillationwas distilled off under reduced pressure
  7. extractionExtraction with ethyl acetate
  8. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  9. filtrationsubjected to filtration
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe crude product thus obtained
  12. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8908ff01582841279a7dd5012f7935ea
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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