Iodine → HCID 58186771, compound

HRID 481404

Reaction equation

HRID 481404 reaction equation
C(O[CH:4]([O:8][CH2:9][CH3:10])[O:5]CC)C.[CH3:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([C:22](=O)C)[CH:16]=[CH:15]2.II>C(O)C.[N+]([O-])([O-])=O.[Ag+]>[CH2:9]([O:8][C:4](=[O:5])[CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:22])[CH:18]=2)[CH:13]=1)[CH3:10]

Participants

6

Reactant 3

HCID 807IodineHCID 31214Ethyl orthoformateHCID 5980856'-Methyl-2'-acetonaphthone

Product 1

HCID 58186771HCID 58186771, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Triethylorthoformate (1.5 ml) and 1-(6-methylnaphthalen-2-yl)ethanone (1.0 mmol) were dissolved in ethanol (4 ml). To the reaction mixture were added AgNO3 (2.1 mmol) and I2 (1.05 mmol) and the reaction mixture was heated to 80° C. for 20 hours. The reaction mixture was cooled to ambient temperature and concentrated to dryness. The residue was diluted eith EtOAc and filtered through celite. The combined organics were washed with saturated sodium bicarbonate solution and brine. The organic layer was then dried over MgSO4, filtered and concentrated to dryness. The crude residue was chromatographed on silica gel using 5% EtOAc in hexanes as the eluant to yield the title compound (50).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated to dryness
  3. additionThe residue was diluted eith EtOAc
  4. filtrationfiltered through celite
  5. washThe combined organics were washed with saturated sodium bicarbonate solution and brine
  6. dry with materialThe organic layer was then dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude residue was chromatographed on silica gel using 5% EtOAc in hexanes as the eluant

Sources & evidence

ORD record
ord-dcbbce4be8e2461eb5ab97dbecd74661
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Linked notes

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