Methyl iodide → HCID 22145398, compound

HRID 1825354Notes

Reaction equation

HRID 1825354 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, compound

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 , 4.5 mM). Sodium hydride (0.17 g 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 cave 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 cave the title compound (0.157 g, 22%)

Sources & evidence

ORD record
ord-73ff35789e3b402288a5aa8580da360b
Source dataset
uspto-grants-2006_05
Patent number
US07045619B2

Reaction notes

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