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

HRID 1773774Notes

Reaction equation

HRID 1773774 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]>CCO>[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

4

Reactant 2

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

Product 1

HCID 178469067HCID 178469067, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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. for 16 hours and the solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 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; AcOEt in DCM 0/100 to 20/80)
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-d8ec25082ee7431d808c2415512b2a50
Source dataset
uspto-grants-2016_02
Patent number
US09255103B2

Reaction notes

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