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

HRID 1110677Notes

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-pyridyl-oxy)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-b622aac4607c455289404d59b8ea032a
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04976773

Reaction notes

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