2,5-Dimethoxytetrahydrofuran → ethyl 5-(1H-pyrrol-1-yl)-1-t-butyl-1H-pyrazole-4-carboxylate

HRID 2261320Notes

Reaction equation

HRID 2261320 reaction equation
[NH2:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].CO[CH:18]1[CH2:22][CH2:21][CH:20](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[N:6]([C:7]([CH3:8])([CH3:9])[CH3:10])[N:5]=[CH:4][C:3]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:18]=[CH:22][CH:21]=[CH:20]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 13809946ethyl 5-amino-1-(tert-butyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 57736366ethyl 5-(1H-pyrrol-1-yl)-1-t-butyl-1H-pyrazole-4-carboxylateYield 85.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.45 g of ethyl 5-amino-1-t-butyl-1H-pyrazole-4-carboxylate was dissolved in 60 ml of acetic acid, and 7.93 g of 2,5-dimethoxytetrahydrofuran was then added. The mixture was heated to reflux for 2 hours. The reaction mixture was concentrated under reduced pressure. After water was added, the residue was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 8.95 g of ethyl 5-(1H-pyrrol-1-yl)-1-t-butyl-1H-pyrazole-4-carboxylate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionAfter water was added
  5. extractionthe residue was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-de6d3e431d434b55b9eb46e49ffbc617
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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