Hydrochloric Acid → HCID 57736383, compound

HRID 2261356Notes

Reaction equation

HRID 2261356 reaction equation
[OH:1][C:2]([C:5]1[O:9][N:8]=[C:7]([CH:10]=[C:11]([C:14]#[N:15])[C:12]#[N:13])[CH:6]=1)([CH3:4])[CH3:3].[CH:16]([Mg]Br)([CH3:18])[CH3:17].Cl>O1CCOCC1.O1CCCC1.[Cu]I>[OH:1][C:2]([C:5]1[O:9][N:8]=[C:7]([CH:10]([CH:11]([C:12]#[N:13])[C:14]#[N:15])[CH:16]([CH3:18])[CH3:17])[CH:6]=1)([CH3:4])[CH3:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 57736335{[5-(1-Hydroxy-1-methylethyl)-isoxazol-3-yl]methylidene}malononitrileHCID 178418365HCID 178418365, compound

Product 1

HCID 57736383HCID 57736383, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

1.02 g of {[5-(1-hydroxy-1-methylethyl)-isoxazol-3-yl]methylidene}malononitrile was dissolved in 50 ml of 1,4-dioxane. Thereto, 0.05 g of copper(I) iodide was added and 15 ml of a 1 M solution of i-propylmagnesium bromide in tetrahydrofuran was then added under ice-cooling. The mixture was stirred for 1 hour under ice-cooling. The reaction mixture was added to 0.1 M hydrochloric acid and then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.40 g of {1-[5-(1-hydroxy-1-methylethyl)-isoxazol-3-yl]-2-methylpropyl}malononitrile.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-48cd402c0a5e4dadaddae95db87607d9
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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