Dimethyl itaconate → HCID 118208947, compound

HRID 595220Notes

Reaction equation

HRID 595220 reaction equation
N12CCCN=C1CCCCC2.[CH2:12]=[C:13]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:14]([O:16][CH3:17])=[O:15].[I:23][C:24]1[CH:25]=[N:26][NH:27][CH:28]=1>C(#N)C.O>[I:23][C:24]1[CH:25]=[N:26][N:27]([CH2:12][CH:13]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:14]([O:16][CH3:17])=[O:15])[CH:28]=1

Participants

6

Reactant 3

HCID 69240Dimethyl itaconateHCID 770224-IodopyrazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 118208947HCID 118208947, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (753 mg, 3 mmol) was added to a stirred mixture of dimethyl 2-methylenesuccinate (158 mg, 1.00 mmol) and 4-iodo-1H-pyrazole (194 mg, 1.00 mmol) in acetonitrile (2 mL) and the mixture was stirred at room temperature under N2 for 12 hours. The mixture was diluted with water and extracted with EtOAc. The EtOAc layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by prep-TLC on silica gel (petroleum ether/EtOAc) to afford dimethyl 2-((4-iodo-1H-pyrazol-1-yl)methyl)succinate. MS ESI calcd. for C10H14IN2O4 [M+H]+ 353, found 353. 1H NMR (400 MHz, CDCl3) δ 7.52 (s, 1H), 7.39 (s, 1H), 4.55-4.36 (m, 2H), 3.72 (s, 3H), 3.68 (s, 3H), 3.42-3.33 (m, 1H), 2.70-2.47 (m, 2H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe EtOAc layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by prep-TLC on silica gel (petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-800ea8c79c5d4b9c9fdebb4bec484321
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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