Water → HCID 178466003, compound

HRID 392583Notes

Reaction equation

HRID 392583 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]([C:16]1[N:17]=[CH:18][N:19](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:20]=1)=[O:15])[CH:8]=[CH:7]2)[CH3:2].[CH:40]([Mg]Cl)([CH3:42])[CH3:41].[Cl-].[NH4+].O>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]([C:16]1[N:17]=[CH:18][NH:19][CH:20]=1)([OH:15])[CH:40]([CH3:42])[CH3:41])[CH:8]=[CH:7]2)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 22664967HCID 22664967, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 178466003HCID 178466003, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(6-Ethoxynaphthalen-2-yl)-(1-trityl-1H-imidazol-4-yl)ketone (3.0 g) was dissolved in THF (45 ml) and a solution (2 M, 4 ml) of isopropyl magnesium chloride in THF was added dropwise under ice-cooling. The mixture was stirred at room temperature for 30 min and saturated aqueous solution (20 ml) of ammonium chloride and water (20 ml) were added. The mixture was extracted with ethyl acetate and the extract was washed with saturated brine, dried and concentrated. The residue was crystallized from ethyl acetate-diisopropyl ether to give the title compound (1.72 g) as a colorless powder. Crystallization mother liquor was purified by silica gel chromatography (eluate, hexane-ethyl acetate=1:2) to give the title compound (0.43 g).

Workup

  1. temperaturecooling
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was crystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-99cb3a8d88904992bd31ab98bb1c1a72
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Reaction notes

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