Imidazole → HCID 178487496, compound

HRID 1368530Notes

Reaction equation

HRID 1368530 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH:12]([OH:14])[CH3:13])=[C:7]([O:15][CH3:16])[CH:6]=[CH:5]2.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18].[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1>CN(C=O)C>[Si:21]([O:14][CH:12]([C:8]1[C:7]([O:15][CH3:16])=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([C:12]([C:29]1[N:25]=[CH:26][NH:27][CH:28]=1)([OH:14])[CH:8]([CH3:9])[CH3:7])=[CH:3]2)[CH3:13])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22018355HCID 22018355, compound

Product 1

HCID 178487496HCID 178487496, compoundYield 170.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(6-Bromo-2-methoxynaphthalen-1-yl)ethanol (18.57 g) and tert-butyldimethylchlorosilane (11.40 g) were dissolved in DMF (300 ml). To the solution was added imidazole (13.20 g), and the mixture was stirred at room temperature for 14 h. The reaction mixture was concentrated, and to the residue were added water and ethyl acetate. The organic layer was washed with water and saturated solution of sodium chloride, dried and concentrated to give the titled compound (25.58 g) as a colorless liquid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionto the residue were added water and ethyl acetate
  3. washThe organic layer was washed with water and saturated solution of sodium chloride
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-032ea70da02048678f566e303dcd03e4
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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