1,4-Dioxane hydrochloride → HCID 66974441, compound

HRID 1782275Notes

Reaction equation

HRID 1782275 reaction equation
[C:1]([CH:3]([CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1)=O)[C:4]([O:6][CH3:7])=[O:5])#[N:2].O1CCOCC1.[ClH:29]>>[Cl:29][C:1]1[NH:2][C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66974584HCID 66974584, compound

Product 1

HCID 66974441HCID 66974441, compound

Procedure

14% Hydrogen chloride-1,4-dioxane solution (50 mL) was added to methyl 2-cyano-4-(4-cyclohexylphenyl)-4-oxobutanoate (12.1 g) and the mixture was stirred at room temperature for 8 hr and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether and collected by filtration to give a nearly 1:1 mixture (3.41 g) of the title compound and methyl 2-amino-5-(4-cyclohexylphenyl)-3-furoate. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:2) to give the title compound as crystals (yield 0.64 g, 5%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from diisopropyl ether
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-9bde0efe4776456b93ee9a0bc799c1cb
Source dataset
uspto-grants-2009_03
Patent number
US07498337B2

Reaction notes

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