Imidazole → HCID 22324681, compound

HRID 496427Notes

Reaction equation

HRID 496427 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.FC(F)(F)S(O[CH2:14][C:15]([CH3:37])([O:17][C:18]1[CH:27]=[CH:26][C:25]2[C:24](=[O:28])[CH2:23][CH2:22][CH2:21][C:20]=2[C:19]=1[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:16])(=O)=O>C(#N)C>[N:3]1([CH2:14][C:15]([CH3:37])([CH3:16])[O:17][C:18]2[C:19]([CH2:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[C:20]3[C:25](=[CH:26][CH:27]=2)[C:24](=[O:28])[CH2:23][CH2:22][CH2:21]3)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 22324798HCID 22324798, compound

Product 1

HCID 22324681HCID 22324681, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of sodium hydride (60% dispersion in oil, 32 mg, 0.81 mmol), acetonitrile (0.4 mL), and imidazole (275 mg, 4.0 mmol) was stirred at room temperature for 10 min, whereupon a solution of 2-methyl-2-{[5-oxo-1-(2-phenylethyl)-5,6,7,8-tetrahydro-2-naphthalenyl]oxy}propyl trifluoromethane-sulfonate (190 mg, 0.40 mmol) in acetonitrile (0.8 mL) was added. The resulting mixture was stirred at reflux for 20 min and was then concentrated. The residue was purified by dry-flash column chromatography (SiO2, 1-10% 2-propanol-dichloromethane) to give 6-[2-(1H-imidazol-1-yl)-1,1-dimethylethoxy]-5-(2-phenylethyl)-3,4-dihydro-1(2H)-naphthalenone as a colorless oil, 126 mg, 92% yield. NMR spectrum was consistent with structure. MS EI: M+• 388.2149 (M+• 388.2151).

Workup

  1. additionwas added
  2. temperatureat reflux for 20 min
  3. concentrationwas then concentrated
  4. customThe residue was purified by dry-flash column chromatography (SiO2, 1-10% 2-propanol-dichloromethane)

Sources & evidence

ORD record
ord-a8f3161de67747a8b7b77d1cff686688
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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