1-Iodopropane → HCID 66958661, compound

HRID 2283779Notes

Reaction equation

HRID 2283779 reaction equation
[CH2:1](I)[CH2:2][CH3:3].[O-]CC.[Na+].[CH2:9]([C:11]1[NH:15][N:14]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:12]=1)[CH3:10]>C(O)C>[CH2:2]([C:1]1[N:15]([CH2:11][CH2:9][CH3:10])[N:14]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:12]=1)[CH3:3]

Participants

5

Reactant 3

HCID 336431-Iodopropane2×HCID 2723922Sodium ethoxide2×HCID 80276141H-Pyrazole-3-carboxylic acid, 5-ethyl-, ethyl ester

Product 1

HCID 66958661HCID 66958661, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Propyl iodide (0.43 mL, 4.46 mmol) and a solution of sodium ethoxide in ethanol (21%, 0.95 g, 3.27 mmol) were added to a solution of ethyl 5-ethyl-1H-pyrazole-3-carboxylate (0.5 g, 2.97 mmol) in ethanol (5 mL) at ambient temperature. The reaction was stirred overnight, and additional propyl iodide (0.05 mL) and sodium ethoxide in ethanol (21%, 0.1 g) were added. After 3 hours, the solvent was removed under reduced pressure and the residue was partitioned between an aqueous sodium chloride solution and methyl tert-butyl ether. The aqueous phase was extracted with methyl tert-butyl ether twice. The organic phases were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield impure ethyl 5-ethyl-1-propyl-1H-pyrazole-3-carboxylate.

Workup

  1. waitAfter 3 hours
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was partitioned between an aqueous sodium chloride solution and methyl tert-butyl ether
  4. extractionThe aqueous phase was extracted with methyl tert-butyl ether twice
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dd2c0c8cebb14986ac4bb935bfe0192a
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

Loading…