Ammonium Chloride → HCID 118308685, compound

HRID 923479Notes

Reaction equation

HRID 923479 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:4]=[N:3]1.[CH3:14][Mg]Br.C(OCC)C.[Cl-].[NH4+]>C1COCC1>[OH:13][C:7]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1)([CH3:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 47002973ethyl 2-(1-methyl-1H-pyrazol-4-yl)-2-oxoacetateHCID 178467822HCID 178467822, compound

Product 1

HCID 118308685HCID 118308685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, to a solution of 500 mg of ethyl (1-methyl-1H-pyrazol-4-yl)(oxo)acetate that had been cooled in a dry ice-acetone bath in 7.5 ml of THF was added 1.56 ml of a 3.0 M methyl magnesium bromide/diethyl ether solution, followed by stirring for 1 hour. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 302 mg of ethyl 2-hydroxy-2-(1-methyl-1H-pyrazol-4-yl)propanoate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e5f4da5c04e240a18a0be4a11b6e794c
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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