Triethylamine → (2,3,4-Trimethoxy-6-methylphenyl)(3-chloro-5-trifluoromethyl-4-pyridyl)methanol

HRID 1835416Notes

Reaction equation

HRID 1835416 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[C:5]([CH3:13])[C:4]=1[CH:14]([C:16]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][N:19]=[C:18](Cl)[C:17]=1[Cl:27])[OH:15].C(N(CC)CC)C>[C].[Pd].CO>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[C:5]([CH3:13])[C:4]=1[CH:14]([C:16]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][N:19]=[CH:18][C:17]=1[Cl:27])[OH:15]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 12151301(2,3,4-Trimethoxy-6-methylphenyl)(2,3-dichloro-5-trifluoromethyl-4-pyridyl)methanol

Product 1

HCID 12151302(2,3,4-Trimethoxy-6-methylphenyl)(3-chloro-5-trifluoromethyl-4-pyridyl)methanolYield 70%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2.1 g of 5% palladium carbon was added to a methanol 200 ml solution of 24.8 g (58.1 mmol) of (2,3,4-trimethoxy-6-methylphenyl)(2,3-dichloro-5-trifluoromethyl-4-pyridyl)methanol obtained in step (a) and 9.50 ml (68.2 mmol) of triethylamine, followed by stirring under hydrogen atmosphere for 4 hours. The mixture was subjected to filtration, 50 ml of water was added thereto, and methanol was distilled off under reduced pressure. The aqueous layer was extracted with ethyl acetate, and 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 15.9 g (yield 70%) of (2,3,4-trimethoxy-6-methylphenyl)(3-chloro-5-trifluoromethyl-4-pyridyl)methanol (m.p. 102-105° C.).

Workup

  1. filtrationThe mixture was subjected to filtration, 50 ml of water
  2. additionwas added
  3. distillationmethanol was distilled off under reduced pressure
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. filtrationsubjected to filtration
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe crude product thus obtained
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-52fe4334d0264505bf6cad405e430493
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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