Sodium Hydroxide → 1,5-Diethyl-1H-pyrazole-3-carboxylic acid

HRID 1825341Notes

Reaction equation

HRID 1825341 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][CH3:9])=[CH:6][C:5]([C:10]([O:12]CC)=[O:11])=[N:4]1)[CH3:2].[OH-].[Na+].C(OCC)(=O)C.O>C(O)C>[CH2:1]([N:3]1[C:7]([CH2:8][CH3:9])=[CH:6][C:5]([C:10]([OH:12])=[O:11])=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 22145420Ethyl 1,5-diethylpyrazole-3-carboxylateHCID 22728543Water ethylacetate

Product 1

HCID 221453751,5-Diethyl-1H-pyrazole-3-carboxylic acidYield 82.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1,5-diethylpyrazole-3-carboxylate (20.7 g) in ethanol (250 ml) was treated with 2.5M aqueous NaOH (50.6 ml), and the mixture was stirred overnight. A further 4.2 ml of 2.5M NaOH was then added and stirring continued for a further 1 hour. The mixture was then poured into ethyl acetate/water. The mixture was shaken vigorously and the aqueous phase removed. The pH of the aqueous phase was adjusted to 2.0 using 1M aqueous HCl and saturated with NaCl. The aqueous layer was then extracted with 20% toluene/80% THF (5×100 ml). The combined organic extracts were dried over MgSO4 and evaporated in vacuo. The residue was triturated with hexane/diethyl ether to give the acid as a solid (14.69 g); υmax(CH2Cl2) 3450, 2750, 2596, 1697, cm−1; δ(CDCl3) 1.31 (3H, t, J 7 Hz), 1.44 (3H, t,J 7 Hz) 2.64 (2H, q, J 7 Hz), 4.20 (2H, q, J 7 Hz), 6.64 (1H,s) ppm.

Workup

  1. stirringstirring
  2. waitcontinued for a further 1 hour
  3. stirringThe mixture was shaken vigorously
  4. customthe aqueous phase removed
  5. extractionThe aqueous layer was then extracted with 20% toluene/80% THF (5×100 ml)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. customevaporated in vacuo
  8. customThe residue was triturated with hexane/diethyl ether

Sources & evidence

ORD record
ord-b95e053a23db4b2ba3920b7037546073
Source dataset
uspto-grants-2006_05
Patent number
US07045619B2

Reaction notes

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