Ammonium Chloride → HCID 178437262, compound

HRID 1368545Notes

Reaction equation

HRID 1368545 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH:12]=[CH2:13])=[C:7]([O:14][CH3:15])[CH:6]=[CH:5]2.C([Li])CCC.[NH:21]1[CH:25]=[C:24]([C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])[N:23]=[CH:22]1.[Cl-].[NH4+]>C1COCC1.CCCCCC.O>[CH2:12]([C:8]1[C:7]([O:14][CH3:15])=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([C:26]([C:24]1[N:23]=[CH:22][NH:21][CH:25]=1)([OH:30])[CH:27]([CH3:29])[CH3:28])=[CH:3]2)[CH3:13]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 220184616-Bromo-1-ethenyl-2-methoxynaphthaleneHCID 178418339ButyllithiumHCID 178450295HCID 178450295, compound

Product 1

HCID 178437262HCID 178437262, compoundYield 86.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

6-Bromo-1-ethenyl-2-methoxynaphthalene (1.20 g) was dissolved in THF (12 ml). To the solution was added dropwise a solution of n-butyllithium in hexane (1.6M: 3.4 ml) at −70° C., and the mixture was stirred for 30 min. A solution of 1-(1H-imidazol-4-yl)-2-methyl-1-propanone (1.73 g) in THF (10 ml) was stirred for 40 min, and the temperature of the mixture was elevated to room temperature. To the reaction mixture were added an aqueous solution of ammonium chloride (10 ml) and water (10 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried and concentrated. The residue was crystallized from ethyl acetate to give the titled compound (1.28 g) as a colorless powder. Mother liquor was purified by silica gel column chromatography (eluent, hexane-ethyl acetate=1:1) followed by recrystallization from ethyl acetate-diisopropyl ether to give the titled compound (0.23 g).

Workup

  1. customwas elevated to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-784bff96f19e42e6ab20116c61687cb9
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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