Hydrazine hydrate (1:1) → HCID 178469067, compound

HRID 2046166Notes

Reaction equation

HRID 2046166 reaction equation
O.[NH2:2][NH2:3].[CH2:4]([O:6][C:7](=[O:21])[C:8](=O)[CH2:9][C:10](=O)[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:5]>>[CH2:4]([O:6][C:7]([C:8]1[NH:2][N:3]=[C:10]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=1)=[O:21])[CH3:5]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 574350862,4-Dioxo-5-phenoxy-pentanoic acid ethyl ester

Product 1

HCID 178469067HCID 178469067, compoundYield 98%

Conditions

Temperature
80 °C

Procedure

Hydrazine hydrate (0.27 mL, 2.76 mmol) was added to a stirred solution of 2,4-dioxo-5-phenoxy-pentanoic acid ethyl ester (0.69 g, 2.76 mmol in EtOH (3 mL)). The mixture was stirred at 80° C. overnight. The solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; DCM in AcOEt 0/100 to 20/80). The desired fractions were collected and the solvents evaporated in vacuo to yield 5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (0.66 g, 98% yield) as a yellow oil.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe crude product was purified by flash column chromatography (silica; DCM in AcOEt 0/100 to 20/80)
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-35299c73370e447e881a08b6e2c12f00
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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