Lithium Hydroxide → HCID 118208557, compound

HRID 595221Notes

Reaction equation

HRID 595221 reaction equation
[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH:8]([CH2:13][C:14]([O:16]C)=[O:15])[C:9]([O:11]C)=[O:10])[CH:6]=1.[OH-].[Li+]>C1COCC1.O.O>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH:8]([CH2:13][C:14]([OH:16])=[O:15])[C:9]([OH:11])=[O:10])[CH:6]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 118208947HCID 118208947, compound

Product 1

HCID 118208557HCID 118208557, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of dimethyl 2-((4-iodo-1H-pyrazol-1-yl)methyl)succinate (200 mg, 0.61 mmol) and lithium hydroxide (40 mg, 1.80 mmol) in THF/water (4 mL/1 mL) was stirred at 60° C. for 12 hours. After cooling to room temperature, 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 to afford 2-((4-iodo-1H-pyrazol-1-yl)methyl)succinic acid. MS ESI calc'd. for C8H10IN2O4 [M+H]+ 325. found 325. 1H NMR (400 MHz, CD3OD) δ 7.76 (s, 1H), 7.50 (s, 1H), 4.60-4.48 (m, 2H), 3.46-3.38 (m, 1H), 2.83-2.73 (m, 1H), 2.60-2.51 (m, 1H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b6bd6ebbd8c9493bade0857af8f97602
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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