Imidazole → HCID 22998561, compound

HRID 1166525Notes

Reaction equation

HRID 1166525 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[C:27]1([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:32]=[CH:31][C:30]([CH2:33][O:34][C:35]2[CH:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[CH2:41][CH:40]([CH2:45][CH2:46]O)[CH2:39][CH2:38]3)=[CH:29][CH:28]=1>C1COCC1.O>[C:27]1([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:32]=[CH:31][C:30]([CH2:33][O:34][C:35]2[CH:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[CH2:41][CH:40]([CH2:45][CH2:46][I:25])[CH2:39][CH2:38]3)=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 22998673HCID 22998673, compound

Product 1

HCID 22998561HCID 22998561, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of triphenylphosphine (12.5 g) in THF (200 ml) were successively added imidazole (3.25 g) and iodine (12.1 g). A solution of 6-(4-biphenylyl) methoxy-2-(2-hydroxyethyl)tetralin (13.15 g) in THF (100 ml) was added to the reaction mixture at room temperature. The reaction mixture was stirred at room temperature for 5 min, diluted with water, and extracted with ethyl acetate. The organic layer was washed with aqueous sodium thiosulfate and saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by silica gel column chromatography (eluent; toluene) to obtain the titled compound (13.2 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with aqueous sodium thiosulfate and saturated aqueous sodium chloride
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent; toluene)

Sources & evidence

ORD record
ord-3fb494f1cc474be994fb7fb1e780087c
Source dataset
uspto-grants-2003_09
Patent number
US06613805B2

Reaction notes

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