Water → HCID 178487492, compound

HRID 1368510Notes

Reaction equation

HRID 1368510 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]=2)=[O:7])[N:3]=[CH:2]1.[CH:20]([Mg]Cl)([CH3:22])[CH3:21].[Cl-].[NH4+].O>C1COCC1>[NH:1]1[CH:5]=[C:4]([C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]=2)([OH:7])[CH:20]([CH3:22])[CH3:21])[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 178418918HCID 178418918, compoundHCID 178487490HCID 178487490, compound

Product 1

HCID 178487492HCID 178487492, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

(1H-Imidazol-4-yl)-(6-methoxynaphthalen-2-yl)ketone (6.50 g) was dissolved in THF (120 ml), and the solution was cooled to −10° C. To the solution was slowly added dropwise a solution of isopropyl magnesium chloride in THF (2.0 M; 38.7 ml), and the mixture was stirred at −10° C. for 30 min. To the reaction mixture was added saturated aqueous solution of ammonium chloride and water. The mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous solution of sodium chloride, dried and concentrated. The residue was purified by silica gel column chromatography (eluent, chloroform:methanol=20:1→10:1). Recrystallization from ethyl acetate gave the titled compound (5.04 g) as a colorless crystalline powder.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous solution of sodium chloride
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent, chloroform:methanol=20:1→10:1)
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-e95ae7f9ea34473b9c5e4a42c73f0396
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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