Lithium hydroxide, monohydrate → HCID 77013264, compound

HRID 2206873Notes

Reaction equation

HRID 2206873 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][O:6][N:7]=[C:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[CH3:9])C.O.[OH-].[Li+]>O1CCCC1.O>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:8](=[N:7][O:6][CH2:5][C:4]([OH:17])=[O:3])[CH3:9])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 131735869HCID 131735869, compound

Product 1

HCID 77013264HCID 77013264, compoundYield 37.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl({[1-(4-fluorophenyl)ethylidene]amino}oxy)acetate (8.7 g) in a mixture of 50 ml of tetrahydrofuran and 10 ml of water was added, at 20° C., lithium hydroxide monohydrate (2.3 g) and the mixture was stirred at this temperature for 18 hours. Subsequently, the mixture was stirred into ice-cold 10% hydrochloric acid and extracted twice with ethyl acetate (50 ml each time). The combined organic phases were dried over sodium sulphate and concentrated. Purification by column chromatography on silica gel with a solvent gradient from 0:100 methanol/dichloromethane to 60:0 methanol/dichloromethane gave ({[1-(4-fluorophenyl)ethylidene]amino}oxy)acetic acid (2.9 g).

Workup

  1. additionwas added, at 20° C.
  2. extractionextracted twice with ethyl acetate (50 ml each time)
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel with a solvent gradient from 0:100 methanol/dichloromethane to 60:0 methanol/dichloromethane

Sources & evidence

ORD record
ord-028a7605c8ce4555a770ad44d23562f1
Source dataset
uspto-grants-2016_06
Patent number
US09375009B2

Reaction notes

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