Water → 2-(4-(3-Chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propionic acid 2-oxopropyl ester

HRID 1591019Notes

Reaction equation

[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19]([OH:21])=[O:20])=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH:25]1(NC2CCCCC2)[CH2:30]CCC[CH2:26]1.[OH2:38]>CN(C)C=O>[O:38]=[C:25]([CH3:30])[CH2:26][O:20][C:19](=[O:21])[CH:18]([O:17][C:16]1[CH:23]=[CH:24][C:13]([O:12][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=2)=[CH:14][CH:15]=1)[CH3:22]

Participants

Conditions

Temperature: 60 °C

Procedure

2-(4-(3-Chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy) propionic acid (3.62 g) was dissolved in dimethylformamide (50 ml) and the solution was stirred with an addition of dicyclohexylamine (2.2 ml). The mixture was further stirred at a temperature of 60° C. for 3 hours. To the reaction mixture, 100 ml of water was added, followed by extracting with toluene. After washing with water, the mixture was dried over anhydrous magnesium sulfate, the solvent was distilled off under a reduced pressure, and the resultant oily product was subjected to silica gel medium pressure column chromatography (n-hexane/ethyl acetate =9/1 v/v%) to obtain 4.00 g of the title compound in the form of a colorless oily product (yield =96%).

Workup

extractionby extracting with toluene
washAfter washing with water
dry with materialthe mixture was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record: ord-910aab7c9afd41d9ba56cdc66a3ca52e
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05205855

Reaction notes

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