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

HRID 242428Notes

Reaction equation

HRID 242428 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.ClC1C(Cl)=C([Li])C(C(F)(F)F)=C(Cl)N=1.[CH3:40][O:41][C:42]1[C:49]([O:50][CH3:51])=[C:48]([O:52][CH3:53])[CH:47]=[C:46]([CH3:54])[C:43]=1[CH:44]=[O:45]>C(OCC)C.C1(C)C=CC=CC=1.O>[CH3:40][O:41][C:42]1[C:49]([O:50][CH3:51])=[C:48]([O:52][CH3:53])[CH:47]=[C:46]([CH3:54])[C:43]=1[CH:44]([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:45]

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 896832,3,4-Trimethoxy-6-methylbenzaldehydeHCID 27606902,3,6-Trichloro-5-(trifluoromethyl)pyridineHCID 178418339ButyllithiumHCID 178506749HCID 178506749, compound

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 mol/l 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., and a solution having 6.0 g (24 mmol) of 2,3,6-trichloro-5-trifluoromethylpyridine dissolved in 8 ml of diethyl ether was added, followed by stirring for 25 minutes to prepare 2,3,6-trichloro-5-trifluoromethyl-4-pyridyllithium, and then a solution having 5.0 g (24 mmol) of 2,3,4-trimethoxy-6-methylbenzaldehyde dissolved in 12 ml of toluene was added, followed by stirring for 1 hour. 30 ml of water was added to the mixture to terminate the reaction, and the aqueous layer was extracted with ethyl acetate. 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 (melting point 131 to 135° C.).

Workup

  1. additionwas added
  2. stirringby stirring for 25 minutes
  3. additionwas added
  4. stirringby stirring for 1 hour
  5. customto terminate
  6. customthe reaction
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. dry with materialThen, the 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-1dac08843a474b1e98e89f6d86dd6abd
Source dataset
uspto-grants-2014_02
Patent number
US08653113B2

Reaction notes

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