Butyl iodide → HCID 18376536, compound

HRID 2300578Notes

Reaction equation

HRID 2300578 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]([C:13]([CH3:17])([CH3:16])[CH:14]=[O:15])=[CH:6][C:5]2=[O:18].I[CH2:20][CH2:21][CH2:22][CH3:23]>CC#N.[Ag]>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]([C:13]([CH3:16])([CH3:17])[CH:14]=[O:15])=[CH:6][C:5]2=[O:18])[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 10962Butyl iodideHCID 18376526HCID 18376526, compound2×

Product 1

HCID 18376536HCID 18376536, compound

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(6-Hydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-2-methylpropanal (compound 3 prepared in step II above) (125 mg, 0.52 mmol) and freshly prepared Ag2O (240 mg, 1.04 mmol) in CH3CN was ultrasonicated for 2 min to disperse the silver salt. Iodobutane (120 μL, 1.05 mmol) was added and the mixture was stirred over night at room temperature. The mixture was filtered on Celite and was washed with EtOAc. The crude product was purified on silica gel with hexane:EtOAc 4:1 but failed to yield pure material. The product was further purified on RP-HPLC. Yield: 53 mg (34%). 1H NMR (400 MHz, CDCl3) δ 0.99 (tr., 3H), 1.40 (s, 6 H), 1.52 (sext., 2 H), 1.82 (quint., 2 H), 4.11 (tr., 2H), 6.87 (s, 1 H), 7.18 (dd, 1 H), 7.48 (d, 1 H), 8.00 (dd, 1 H), 9.72 (s, 1 H).

Workup

  1. customwas ultrasonicated for 2 min
  2. filtrationThe mixture was filtered on Celite
  3. washwas washed with EtOAc
  4. customThe crude product was purified on silica gel with hexane:EtOAc 4:1
  5. customto yield pure material
  6. customThe product was further purified on RP-HPLC

Sources & evidence

ORD record
ord-4cf9b021e71e4961b86fc2db5628c1d3
Source dataset
uspto-grants-2002_12
Patent number
US06498182B2

Reaction notes

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