Water → 2-Methylsulfinyl-naphtho[2,3-b]furan-4,9-dione

HRID 1746927Notes

Reaction equation

HRID 1746927 reaction equation
[CH3:1][S:2][C:3]1[O:7][C:6]2[C:8](=[O:17])[C:9]3[C:14]([C:15](=[O:16])[C:5]=2[CH:4]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3.I(O)(=O)(=O)=[O:19].O>C(#N)C>[CH3:1][S:2]([C:3]1[O:7][C:6]2[C:8](=[O:17])[C:9]3[C:14]([C:15](=[O:16])[C:5]=2[CH:4]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 65185Metaperiodic acidHCID 107766732-Methylthio-naphtho[2,3-b]furan-4,9-dione

Product 1

HCID 568474792-Methylsulfinyl-naphtho[2,3-b]furan-4,9-dioneYield 80.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.5 gram (2.05 mmoles) of 2-methylthio-naphtho[2,3-b]furan-4,9-dione (prepared in example 7) in 20 mL of acetonitrile at room temperature, 0.49 grams (2.15 mmoles) of periodic acid followed by 2 mg of ferric chloride was added. The mixture was stirred for 10 minutes at room temperature, then 50 mL of water was added, and the resulting mixture was evaporated to remove acetonitrile. The remaining aqueous suspension was filtered, and the obtained solid was washed with water and dried under vacuum. The crude solid product was purified with silica gel chromatograph using dichloromethane/ethyl acetate (9:1) as elution solvent. 0.43 grams of product (yield 80%) was obtained and characterized by 1H NMR and mass spectrum. 1H NMR (in DMSO) δ 3.14 (s, 3H), 7.81 (s, 1H), 7.92-7.94 (m, 2H), 8.12-8.17 (m, 2H). Mass (M+H) is 261.

Workup

  1. customat room temperature
  2. additionwas added
  3. customthe resulting mixture was evaporated
  4. customto remove acetonitrile
  5. filtrationThe remaining aqueous suspension was filtered
  6. washthe obtained solid was washed with water
  7. customdried under vacuum
  8. customThe crude solid product was purified with silica gel chromatograph
  9. washas elution solvent

Sources & evidence

ORD record
ord-8539de4edb474764af60123f6ec419b4
Source dataset
uspto-grants-2015_10
Patent number
US09150530B2

Reaction notes

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