HCID 131720095, compound → HCID 15882549, compound

HRID 1597409Notes

Reaction equation

HRID 1597409 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-a148c5d9a56c46069b8ee719d411357b
Source dataset
uspto-grants-2001_09
Patent number
US06294574B1

Reaction notes

Loading…