Hydrochloric Acid → HCID 12111983, compound

HRID 852069Notes

Reaction equation

HRID 852069 reaction equation
[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([CH2:14][CH:15]([O:21][CH:22]([CH3:24])[CH3:23])[C:16]([O:18]CC)=[O:17])[CH:11]=[CH:10][N:9]=1.[OH-].[Na+].Cl>CO.O>[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([CH2:14][CH:15]([O:21][CH:22]([CH3:24])[CH3:23])[C:16]([OH:18])=[O:17])[CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12111982HCID 12111982, compound

Product 1

HCID 12111983HCID 12111983, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of ethyl 3-{2-[2-(2,4-dichlorophenoxy)ethoxy]-4-pyridyl}-2-isopropoxypropanoate (24 mg) in methanol (2 mL) was added 5N aqueous sodium hydroxide solution (0.4 mL), and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was diluted with water, and adjusted to pH 5 with 5N hydrochloric acid. After extracting with ethyl acetate (×2), and the combined organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was purified on a preparative TLC plate to give the title compound as a colorless solid (16 mg).

Workup

  1. extractionAfter extracting with ethyl acetate (×2)
  2. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified on a preparative TLC plate

Sources & evidence

ORD record
ord-588179e217b94564981348501600b8e4
Source dataset
uspto-grants-2007_08
Patent number
US07253178B2

Reaction notes

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