HCID 131720095, compound → HCID 15882549, compound

HRID 265632Notes

Reaction equation

HRID 265632 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:21]2[CH2:25][CH2:24][C@H:23]([C:26]3[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=3)[O:22]2)[CH:6]=[C:7](I)[C:8]=1[O:9][CH2:10][CH2:11][S:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1.[C:38]([Cu])#[N:39]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:21]2[CH2:25][CH2:24][C@H:23]([C:26]3[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=3)[O:22]2)[CH:6]=[C:7]([C:38]#[N:39])[C:8]=1[O:9][CH2:10][CH2:11][S:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 131720095HCID 131720095, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 15882549HCID 15882549, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

trans-2-(3-Methoxy-4-p-chlorophenylthioethoxy-5-iodophenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran (2.35 g, 3.58 mmole) and CuCN (0.358 g, 4.30 mmole) in DMF (20 mL) were heated at 140° C. for 16 hours. The reaction mixture was cooled and quenched with water and extracted with ethyl acetate. The organic layer was washed with water and saturated NaCl solution, dried over MgSO4, filtered and evaporated in vacuo to oil which was purified by column chromatography (silica, 2:1 hexane/ethyl acetate) (1.79 g, 90.0%). 1H NMR (CDCl3): 1.99 (m, 2H); 2.47 (m, 2H); 3.32 (t, 2H); 3.85 (s, 6H), 3.89 (s, 6H); 4.27 (t, 2H); 5.17 (m, 2H); 6.61 (s, 2H); 7.16 (s, 2H); 7.28 (d, 2H); 7.32 (d, 2H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo to oil which
  8. customwas purified by column chromatography (silica, 2:1 hexane/ethyl acetate) (1.79 g, 90.0%)

Sources & evidence

ORD record
ord-f39b5d9d8e914c3ca2d7dcc5eec0c92a
Source dataset
uspto-grants-1997_07
Patent number
US05648486

Reaction notes

Loading…