2-Trimethylsilyl-4,9-dimethoxy-naphtho[2,3-b]furan → 2-Trimethylsilyl-naphtho[2,3-b]furan-4,9-dione

HRID 1746924Notes

Reaction equation

HRID 1746924 reaction equation
[CH3:1][Si:2]([CH3:21])([CH3:20])[C:3]1[O:7][C:6]2[C:8]([O:18]C)=[C:9]3[C:14](=[C:15]([O:16]C)[C:5]=2[CH:4]=1)[CH:13]=[CH:12][CH:11]=[CH:10]3.[N+]([O-])([O-])=O.[NH4+].[Ce]>C(#N)C.O>[CH3:1][Si:2]([CH3:21])([CH3:20])[C:3]1[O:7][C:6]2[C:8](=[O:18])[C:9]3[C:14]([C:15](=[O:16])[C:5]=2[CH:4]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

4

Reactant 2

HCID 105661582-Trimethylsilyl-4,9-dimethoxy-naphtho[2,3-b]furanHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 108496662-Trimethylsilyl-naphtho[2,3-b]furan-4,9-dioneYield 75%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent2×

Procedure

To 1.2 gram (4 mmoles) of crude product 2-trimethylsilyl-4,9-dimethoxy-naphtho[2,3-b]furan in 50 mL of acetonitrile/water (4:1) in ice bath, 4.8 grams (8.7 mmoles) of cerium ammonium nitrate (CAN) solution in 50 mL of acetonitrile/water (1:4) was added dropwise over 10 minutes. The mixture was further stirred in ice bath for 1 hour, and then evaporated to remove acetonitrile. The remaining aqueous suspension was filtered, and the collected solid was washed with water and crystallized in ethanol/water. Pure crystal product was filtered and dried under vacuum. 0.89 grams of product (overall yield 75%) was obtained and characterized by 1H NMR and mass spectrum. 1H NMR (in CDCl3) δ 0.41 (s, 9H), 7.16 (s, 1H), 7.75-7.78 (m, 2H), 8.19-8.26 (m, 2H). Mass (M+H) is 271.

Workup

  1. customevaporated
  2. customto remove acetonitrile
  3. filtrationThe remaining aqueous suspension was filtered
  4. washthe collected solid was washed with water
  5. customcrystallized in ethanol/water
  6. filtrationPure crystal product was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-29294b5d7c3b46f29b09d288c0a78a5b
Source dataset
uspto-grants-2015_10
Patent number
US09150530B2

Reaction notes

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