Tetrahydrofuran → 1-(1H-Imidazol-4-yl)-1-(naphtho[2,1-b]furan-7-yl)-2-methyl-1-propanol

HRID 480467Notes

Reaction equation

HRID 480467 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][O:9][C:8]=1[CH:7]=[CH:6]2.[CH:16]([C:18]1[N:19]=[CH:20][N:21](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:22]=1)=[O:17].[Cl-].[NH4+].[CH2:44]1[CH2:48]OC[CH2:45]1>>[NH:21]1[CH:22]=[C:18]([C:16]([C:3]2[CH:4]=[C:5]3[C:13](=[CH:14][CH:15]=2)[C:12]2[CH:11]=[CH:10][O:9][C:8]=2[CH:7]=[CH:6]3)([OH:17])[CH:44]([CH3:48])[CH3:45])[N:19]=[CH:20]1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 5462224MagnesiumHCID 187690517-Bromonaphtho[2,1-b]furan

Product 1

HCID 1784500551-(1H-Imidazol-4-yl)-1-(naphtho[2,1-b]furan-7-yl)-2-methyl-1-propanol

Conditions

Temperature
0 °C

Procedure

Iodomethyl (0.05 mL) was added to mixture THF (5 mL) and magnesium (turnings, 0.719 g) with stirring. 7-bromonaphtho[2,1-b]furan (6.09 g) was added and the mixture was refluxed for 2 h. The resulting mixture was cooled to 0° C. and a solution of 4-formyl-1-trityl-1H-imidazole (4.71 g) in THF (40 mL) was added. The mixture was stirred at room temperature for 1 h and aq. ammonium chloride was added. The mixture was extracted with ethyl acetate, dried and concentrated. The residue was chromatographed on silica gel (eluent; hexane:ethyl acetate=2:1→1:2) to give the titled compound (2.30 g) as a colorless solid.

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. stirringThe mixture was stirred at room temperature for 1 h
  3. extractionThe mixture was extracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (eluent; hexane:ethyl acetate=2:1→1:2)

Sources & evidence

ORD record
ord-d04ce16a99e44ef1b3727f730ae8150f
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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