Water → HCID 178466003, compound

HRID 1368540Notes

Reaction equation

HRID 1368540 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). To the solution was added dropwise a solution of isopropylmagnesium chloride in THF (2 M, 4 ml) under ice cooling. The reaction mixture was stirred at room temperature for 30 min. To the mixture were added saturated aqueous solution of ammonium chloride (20 ml) and water (20 ml), and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried and concentrated. The residue was crystallized from ethyl acetate-diisopropyl ether to give the titled compound (1.72 g) as a colorless powder. Mother liquor was purified by silica gel chromatography (eluent, hexane-ethyl acetate=1:2) to give the titled compound (0.43 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated sodium chloride solution
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was crystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-d11d5ffe1c144edf801407e635f2ff1b
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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