Ammonium Chloride → HCID 21097232, compound

HRID 2109299Notes

Reaction equation

HRID 2109299 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[CH:5][C:4]=1[CH:14]=[O:15])[CH3:2].[CH3:16][Mg+].[Br-].[NH4+].[Cl-]>C1COCC1.CCOCC>[CH2:1]([C:3]1[N:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:6]=[CH:5][C:4]=1[CH:14]([OH:15])[CH3:16])[CH3:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 105360275-Ethyl-1-phenyl-1H-pyrazole-4-carboxaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 21097232HCID 21097232, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 7.55 (37.7 mmol) of 5-ethyl-1-phenyl-1H-pyrazole-4-carbaldehyde (Example 86) in anhydrous THF (100 mL) under N2 was added over 5 minutes 15.7 (47.1 mmol) of 3.0 M MeMgBr in Et2O. The mixture was warmed to room temperature and stirred for 16 h, then 25 mL of 5% NH4Cl was added and the mixture was extracted with CH2Cl2 (70 mL), and the extract was washed with saturated NaCl (15 mL). The organic layer separated, dried over MgSO4, and concentrated to give 1-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-ethanol (7.91 g). ESI MS m/z 217 [C13H16N2O+H]+.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (70 mL)
  2. washthe extract was washed with saturated NaCl (15 mL)
  3. customThe organic layer separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-626637ff6bfb4075ae369322b41aff50
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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