Potassium Phosphate, Tribasic → HCID 118208705, compound

HRID 595225Notes

Reaction equation

HRID 595225 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[O:7]1[CH2:9][CH:8]1[C:10]([O:12][CH3:13])=[O:11].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O>[OH:7][CH:8]([CH2:9][N:4]1[CH:3]=[C:2]([I:1])[CH:6]=[N:5]1)[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 770224-IodopyrazoleHCID 145751Methyl oxirane-2-carboxylate

Product 1

HCID 118208705HCID 118208705, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-iodo-1H-pyrazole (10 g, 51 mmol), methyl oxirane-2-carboxylate (6.8 g, 67 mmol) and tripotassium phosphate (12 g, 57 mmol) in dioxane (80 mL) was stirred at 90° C. for 4 hours. After cooling to room temperature, the mixture was diluted with water and extracted with DCM. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc) to afford methyl 2-hydroxy-3-(4-iodo-1H-pyrazol-1-yl)propanoate. MS ESI calc'd. for C7H10IN2O3 [M+H]+ 297. found 297. 1H NMR (400 MHz, CDCl3) δ 7.50 (d, J=3.2 Hz, 2H), 4.51-4.46 (m, 3H), 4.27-4.25 (m, 1H), 1.31-1.28 (m, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-4b75e5d361a441b39ba5d294f93f3293
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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