Sodium Hydroxide → HCID 19973419, compound

HRID 1825334Notes

Reaction equation

HRID 1825334 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:15]([O:17]CC)=[O:16])[CH:3]=1.[OH-].[Na+]>C(O)C.C(OCC)(=O)C.O>[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:5]=[C:4]([C:15]([OH:17])=[O:16])[CH:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 22145419Ethyl 5-methyl-1-phenethylpyrazole-3-carboxylate

Product 1

HCID 19973419HCID 19973419, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 5-methyl-1-phenethylpyrazole-3-carboxylate (3.84 g, 14.9 mM) in ethanol (30 ml) with sodium hydroxide (0.6 g 14.9 mM) was stirred at room temperature for 3 days. The mixture was then diluted with ethyl acetate and water and the layers separated. The organic phase was further extracted with water. The combined aqueous extracts were acidified to pH 2.0 with 5M hydrochloric acid and extracted with dichloromethane. The organic extracts were dried (MgSO4) and evaporated to give the title compound (3.24 g, 95%); υmax(CH2Cl2) 1759 and 1699 cm−1; δH(CDCl3) 1.91 (3H, s), 3.16 (2H, t, J7 Hz), 4.31 (2H, t, J7 Hz), 6.54 (1H, s), 6.98-7.10 (2H, m), and 7.20-7.37 (3H, m).

Workup

  1. customthe layers separated
  2. extractionThe organic phase was further extracted with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-8254ec68fdc74393836ce14f87311b14
Source dataset
uspto-grants-2006_05
Patent number
US07045619B2

Reaction notes

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