1,4-Dioxane hydrochloride → HCID 66974441, compound

HRID 2196950Notes

Reaction equation

HRID 2196950 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-1f75be435ab04137a1ec1a49378c41df
Source dataset
uspto-grants-2012_12
Patent number
US08338461B2

Reaction notes

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