Methyl iodide → HCID 22145398, compound

HRID 1452099Notes

Reaction equation

HRID 1452099 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([CH2:10][CH2:11][OH:12])[N:5]=1)(=[O:3])[CH3:2].[CH3:13]I.[H-].[Na+]>COCCOC.[Ag]=O>[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([CH2:10][CH2:11][O:12][CH3:13])[N:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22145372HCID 22145372, compound

Product 1

HCID 22145398HCID 22145398, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Acetyl-1-(2-hydroxyethyl)-5-methylpyrazole (0.63 g, 3.77 mM) in ethylene glycol dimethyl ether (10 ml) was treated with silver oxide (0.87 g, 3.77 mM) and methyl iodide (0.28 ml, 4.5mM). Sodium hydride (0.17g 60% dispersion in oil, 4.14 mM) was added and the mixture stirred for 2 h, then filtered through celite and evaporated. Purification on silica gel eluting with ethyl acetate gave the title compound (0.157 g, 22%): νmax 1681 cm-1 ; δH (CDCl3) 2.32 (3H, s), 2.50 (3H, s), 3.30 (3H, s). 3.78 (2H, t, J5.4 Hz), 4.25 (2H, t, J5.4 Hz), and 6.51 (1H, s); EI m/e 182 (65% ).

Workup

  1. filtrationfiltered through celite
  2. customevaporated
  3. customPurification on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-b177e2332ee94d1cab4182694e42a985
Source dataset
uspto-grants-1997_02
Patent number
US05606051

Reaction notes

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