Triethylamine → 4-(4-Nitrophenoxy)phenyl 2-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propionate

HRID 1591007Notes

Reaction equation

HRID 1591007 reaction equation
Cl.[Cl:2][C:3]1[C:4]([O:13][C:14]2[CH:25]=[CH:24][C:17]([O:18][CH:19]([CH3:23])[C:20](Cl)=[O:21])=[CH:16][CH:15]=2)=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[N+:26]([C:29]1[CH:42]=[CH:41][C:32]([O:33][C:34]2[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=2)=[CH:31][CH:30]=1)([O-:28])=[O:27].C(N(CC)CC)C>O1CCCC1>[Cl:2][C:3]1[C:4]([O:13][C:14]2[CH:25]=[CH:24][C:17]([O:18][CH:19]([CH3:23])[C:20]([O:40][C:37]3[CH:36]=[CH:35][C:34]([O:33][C:32]4[CH:41]=[CH:42][C:29]([N+:26]([O-:28])=[O:27])=[CH:30][CH:31]=4)=[CH:39][CH:38]=3)=[O:21])=[CH:16][CH:15]=2)=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1524504-(4-Nitrophenoxy)phenolHCID 884514024-(3-Chloro-5-trifluoromethyl-2-pyridyloxy)phenoxypropionic acid chloride hydrochloride

Product 1

HCID 144985774-(4-Nitrophenoxy)phenyl 2-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propionateYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-(3-Chloro-5-trifluoromethyl-2-pyridyloxy)phenoxypropionic acid chloride hydrochloride (0.7 g) and 4-(4-nitrophenoxy)phenol (0.5 g) were dissolved in dry tetrahydrofuran (10 ml), and stirred with an addition of triethylamine (0.5 ml) at room temperature for 2 hours. After completion of the reaction, the solvent was evaporated under a reduced pressure and the residue was dissolved in methylene chloride (20 ml), followed by washing with 1 N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, water and saturated aqueous sodium chloride After drying over anhydrous magnesium sulfate, the solvent was evaporated under a reduced pressure and the residue obtained was purified by medium pressure column chromatography by using silica gel, to obtain 4-(4-nitrophenoxy)phenyl 2-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propionate (0.9 g) (oily product).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under a reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride (20 ml)
  4. washby washing with 1 N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, water and saturated aqueous sodium chloride
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customthe residue obtained
  8. customwas purified by medium pressure column chromatography

Sources & evidence

ORD record
ord-ba4921b7c2154265baf15200cb4ddf81
Source dataset
uspto-grants-1993_04
Patent number
US05205855

Reaction notes

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