Diisopropylamine → (2,3,4-Trimethoxy-6-methylphenyl)(2,3,6-trichloro-5-trifluoromethyl-4-pyridyl)methanol

HRID 1835399Notes

Reaction equation

HRID 1835399 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[C:16]([Cl:25])[N:15]=1.[CH3:26][O:27][C:28]1[C:35]([O:36][CH3:37])=[C:34]([O:38][CH3:39])[CH:33]=[C:32]([CH3:40])[C:29]=1[CH:30]=[O:31]>C(OCC)C.C1(C)C=CC=CC=1.O>[CH3:26][O:27][C:28]1[C:35]([O:36][CH3:37])=[C:34]([O:38][CH3:39])[CH:33]=[C:32]([CH3:40])[C:29]=1[CH:30]([C:18]1[C:17]([C:21]([F:24])([F:22])[F:23])=[C:16]([Cl:25])[N:15]=[C:14]([Cl:13])[C:19]=1[Cl:20])[OH:31]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 896832,3,4-Trimethoxy-6-methylbenzaldehydeHCID 27606902,3,6-Trichloro-5-(trifluoromethyl)pyridineHCID 178418339Butyllithium

Product 1

HCID 12151537(2,3,4-Trimethoxy-6-methylphenyl)(2,3,6-trichloro-5-trifluoromethyl-4-pyridyl)methanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

17 ml (25 mmol) of n-butyllithium (1.5 M hexane solution) was dropwise added at 0° C. to a solution having 3.6 ml (25 mmol) of diisopropylamine dissolved in 60 ml of diethyl ether, followed by stirring for 45 minutes. The solution was cooled to −78° C., a solution having 6.0 g (24 mmol) of 2,3,6-trichloro-5-trifluoromethylpyridine dissolved in 8 ml of diethyl ether was added thereto, followed by stirring for 5 minutes, and a solution having 5.0 g (24 mmol) of 2,3,4-trimethoxy-6-methylbenzaldehyde dissolved in 12 ml of toluene was added thereto, followed by stirring for 1 hours. 30 ml of water was added to the mixture to terminate the reaction, the aqueous layer was extracted with ethyl acetate, and then the organic layer was dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure to obtain (2,3,4-trimethoxy-6-methylphenyl)(2,3,6-trichloro-5-trifluoromethyl-4-pyridyl)methanol (m.p. 131-135° C.).

Workup

  1. additionwas added
  2. stirringby stirring for 5 minutes
  3. additionwas added
  4. stirringby stirring for 1 hours
  5. customto terminate
  6. customthe reaction
  7. extractionthe aqueous layer was extracted 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

Sources & evidence

ORD record
ord-5494ef8867d646a689aebd2c9d94778a
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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