Ammonium Chloride → (6-ethoxynaphthalen-2-yl)(1-trityl-1H-imidazol-4-yl)methanol

HRID 392582

Reaction equation

HRID 392582 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][CH3:14])[CH:8]=2)[CH:3]=1.[Mg].[CH:16]([C:18]1[N:19]=[CH:20][N:21]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=1)=[O:17].[Cl-].[NH4+]>C1COCC1.CI.O>[CH2:13]([O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([CH:16]([C:18]1[N:19]=[CH:20][N:21]([C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:22]=1)[OH:17])[CH:11]=[CH:10]2)[CH3:14]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 2368582-Bromo-6-ethoxynaphthaleneHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 5462224Magnesium2×

Product 1

HCID 22664975(6-ethoxynaphthalen-2-yl)(1-trityl-1H-imidazol-4-yl)methanolYield 59.6%

Reagents, catalysts & solvents 3

HCID 6328Methyl iodideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-Bromo-6-ethoxynaphthalene (5.3 g) was dissolved in THF (40 ml) and magnesium (0.515 g) and methyl iodide (one drop) were added and the mixture was vigorously stirred to dissolve magnesium. The reaction mixture was ice-cooled and a solution of 4-formyl-1-tritylimidazole (7 g) in THF (80 ml) was added dropwise over 30 min. The mixture was stirred at room temperature for 1 h. To the reaction mixture were added saturated aqueous solution (40 ml) of ammonium chloride and water (40 ml) and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and concentrated. The residue was washed with ethyl acetate to give (6-ethoxynaphthalen-2-yl)-(1-trityl-1H-imidazol-4-yl)methanol (6.3 g) as a colorless powder. This product (6.3 g) was dissolved in dichloromethane (120 ml) and manganese dioxide (6 g) was added. The mixture was stirred at room temperature overnight. The reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was crystallized from THF-ethyl acetate to give the title compound (5.5 g) as a colorless powder.

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at room temperature for 1 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-bbb43dea9230438392dc61435eab668f
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Linked notes

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