Water → 5-[2-(2-Methoxy-ethoxy)-ethoxy]-2H-pyrazole-3-carboxylic acid ethyl ester

HRID 604444Notes

Reaction equation

HRID 604444 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([OH:11])[CH:10]=1)=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25].O>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([O:11][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1235321-Bromo-3,6-dioxaheptaneHCID 178469379HCID 178469379, compound

Product 1

HCID 574744245-[2-(2-Methoxy-ethoxy)-ethoxy]-2H-pyrazole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3.4 g 5-Hydroxy-2H-pyrazole-3-carboxylic acid ethyl ester and 3 g K2CO3 in 50 ml acetonitrile, 4 g 1-(2-Bromo-ethoxy)-2-methoxy-ethane were added. After stirring for 1 h at RT the reaction was heated to 50° C. for 4 h. Then 50 ml of water were added and the mixture was extracted with DCM (3×100 ml). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica eluting with a DCM/MeOH gradient. Yield: 1 g.

Workup

  1. additionwere added
  2. temperaturewas heated to 50° C. for 4 h
  3. extractionthe mixture was extracted with DCM (3×100 ml)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica eluting with a DCM/MeOH gradient

Sources & evidence

ORD record
ord-386e47f1f2c1409db7a52c93bf2a3cf6
Source dataset
uspto-grants-2011_03
Patent number
US07910606B2

Reaction notes

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