Hydrochloric Acid → HCID 87485559, compound

HRID 1967420Notes

Reaction equation

HRID 1967420 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][CH:11]([CH3:18])[CH2:12]/[CH:13]=[CH:14]/[C:15](=[O:17])[CH3:16].[CH3:19][CH2:20][O:21][C:22]([CH2:24][N+:25]([O-:27])=[O:26])=[O:23].Cl>C(#N)C>[CH2:12]([CH:13]([CH2:14][C:15](=[O:17])[CH3:16])[CH:24]([N+:25]([O-:27])=[O:26])[C:22]([O:21][CH2:20][CH3:19])=[O:23])[CH:11]([CH3:18])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 69379Ethyl nitroacetateHCID 81531DiisopropylethylamineHCID 5462986(3E)-6-Methyl-3-hepten-2-one

Product 1

HCID 87485559HCID 87485559, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diisopropylethylamine (7.9 mL) was added to the acetonitrile solution (50 mL) of (3E)-6-methylhept-3-en-2-one (6.25 g) and nitro ethyl acetate (5 mL) under argon gas atmosphere, and the reaction mixture was stirred at room temperature overnight. 1N hydrochloric acid was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed by water and a saturated aqueous solution of sodium chloride, and dried with anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=95/5→75/25) to obtain the title compound (9.88 g) having the following physical data.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed by water
  3. dry with materiala saturated aqueous solution of sodium chloride, and dried with anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customThe obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=95/5→75/25)

Sources & evidence

ORD record
ord-c314685cc1e749a1b5ad6d686abe61d9
Source dataset
uspto-grants-2013_04
Patent number
US08420810B2

Reaction notes

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