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Pyrazole → 1-(ethoxymethyl)-1H-pyrazole

HRID 46329
Notes
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Reaction equation

HRID 46329 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:12]([O:14][CH2:15]Cl)[CH3:13]>CC(C)=O>[CH2:12]([O:14][CH2:15][N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1)[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 18523Chloromethyl ethyl ether

Product 1

HCID 157143991-(ethoxymethyl)-1H-pyrazoleYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of pyrazole (10 g, 0.150 mol) and potassium carbonate (22.3 g, 0.162 mol) in acetone (200.0 mL), cooled to 0° C. under nitrogen, was added chloromethyl ethyl ether (15.0 mL, 0.162 mol) via syringe over a period of 20 minutes. The reaction was stirred for 30 minutes at 0° C. and then for 2 hours at room temperature. The mixture was filtered, washing the solid with acetone (200.0 mL). The filtrate was carefully concentrated in vacuo (at 400 mbar). The crude material was purified by flash column chromatography eluting with pentane:diethylether (1:1, by volume) to afford the title compound as a colourless oil, 9.3 g, 50% yield.

Workup

  1. waitfor 2 hours at room temperature
  2. filtrationThe mixture was filtered
  3. washwashing the solid with acetone (200.0 mL)
  4. concentrationThe filtrate was carefully concentrated in vacuo (at 400 mbar)
  5. customThe crude material was purified by flash column chromatography
  6. washeluting with pentane:diethylether (1:1, by volume)

Sources & evidence

ORD record
ord-e0460eb9b009438f88eda994a318d272
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541588B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes