Sodium hydride → HCID 64431116, compound

HRID 595223Notes

Reaction equation

HRID 595223 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[N:6][NH:7][CH:8]=1.Cl[CH2:10][C:11](=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1COCC1.O>[I:3][C:4]1[CH:5]=[N:6][N:7]([CH2:10][C:11](=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:8]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetateHCID 770224-Iodopyrazole

Product 1

HCID 64431116HCID 64431116, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (6 g, 250 mmol, 60 wt % in mineral oil) was added to mixture of 4-iodo-1H-pyrazole (10 g, 50 mmol) in THF (200 mL) at room temperature under N2. The mixture was stirred at room temperature for 1 hour. Ethyl 4-chloro-3-oxobutanoate (11.6 g, 75 mmol) was added and the mixture was stirred at room temperature for 12 hours. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether: EtOAc) to afford ethyl 4-(4-iodo-1H-pyrazol-1-yl)-3-oxobutanoate. MS ESI calc'd. for C9H12IN2O3 [M+H]+ 323. found 323. 1H NMR (400 MHz, CDCl3) δ 7.57 (s, 1H), 7.48 (s, 1H), 5.05 (s, 2H), 4.19-4.15 (m, 2H), 3.40 (s, 2H), 1.28-1.24 (m, 3H).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. extractionextracted with EtOAc
  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 column chromatography on silica gel (petroleum ether: EtOAc)

Sources & evidence

ORD record
ord-cfc306dc9b244bab9bc73510143625ad
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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