Potassium Iodide → Tert-butyl (1,2-diethyl-4-pyrazolidinylidene)acetate

HRID 2299111Notes

Reaction equation

HRID 2299111 reaction equation
Cl[CH2:2][C:3]([CH2:12]Cl)=[CH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(=O)([O-])[O-].[K+].[K+].Cl.Cl.[CH2:22]([NH:24][NH:25][CH2:26][CH3:27])[CH3:23].[I-].[K+]>C(#N)C>[CH2:22]([N:24]1[CH2:12][C:3](=[CH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:2][N:25]1[CH2:26][CH3:27])[CH3:23]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 243721,2-Diethylhydrazine dihydrochlorideHCID 18379383Tert-butyl 4-chloro-3-(chloromethyl)-2-butenoate

Product 1

HCID 86584278Tert-butyl (1,2-diethyl-4-pyrazolidinylidene)acetateYield 82.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of tert-butyl 4-chloro-3-(chloromethyl)-2-butenoate (1.2 g, 5.3 mmol), potassium carbonate (4.0 g, 29 mmol), diethylhydrazine dihydrochloride (1.3 g, 8.0 mmol) and potassium iodide (0.86 g, 5.2 mmol) in acetonitrile was stirred at room temperature for 3 days. The mixture was filtered through celite, concentrated and purified by flash chromatography on silica gel eluting ethyl acetate:hexane (20:80, v;v) to give the tert-butyl (1,2-diethyl-4-pyrazolidinylidene)acetate (1.05 g, 82%) as an oil, MS (M+H)+=241.

Workup

  1. filtrationThe mixture was filtered through celite,
  2. concentrationconcentrated
  3. custompurified by flash chromatography on silica gel
  4. washeluting ethyl acetate:hexane (20:80, v;v)

Sources & evidence

ORD record
ord-e3c9e8064684428cba98fb3a9db442bf
Source dataset
uspto-grants-2002_12
Patent number
US06495565B2

Reaction notes

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