Imidazole → HCID 23358296, compound

HRID 234079Notes

Reaction equation

HRID 234079 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[OH:11].N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[O:11][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 133302084-Bromo-1-indanol

Product 1

HCID 23358296HCID 23358296, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the crude 4-bromo-1-indanol (1.02 g) in dimethylformamide (10 ml) were added at an ice temperature imidazole (0.645 g) and tert-butyldimethylsilyl chloride (0.857 g). The reaction mixture was stirred at the same temperature overnight, poured into a saturated aqueous saline solution and extracted with ether. The organic layer was washed with a saturated aqueous saline, dried over sodium sulfate, and the solvent was removed by distillation under reduced pressure. The residual concentrate (1.6 g) was purified by chromatography on a silica gel column to give the title compound (1.51 g).

Workup

  1. additionpoured into a saturated aqueous saline solution
  2. extractionextracted with ether
  3. washThe organic layer was washed with a saturated aqueous saline
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. concentrationThe residual concentrate (1.6 g)
  7. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-4288d54905c64b0ab1df2f79a78dbc6a
Source dataset
uspto-grants-1997_01
Patent number
US05594081

Reaction notes

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