Carbon Disulfide → 3-(p-Anisoyl)-2-ethyl-6-methoxy-benzofuran

HRID 2112288Notes

Reaction equation

HRID 2112288 reaction equation
C(=S)=S.[CH2:4]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:9]=2[CH:10]=1)[CH3:5].[C:17](Cl)(=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.[Sn](Cl)(Cl)(Cl)Cl>O>[C:17]([C:10]1[C:9]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:8]=2[O:7][C:6]=1[CH2:4][CH3:5])(=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 7477p-Anisoyl chlorideHCID 24287Tin tetrachlorideHCID 221436002-Ethyl-6-methoxy-1-benzofuran

Product 1

HCID 529520473-(p-Anisoyl)-2-ethyl-6-methoxy-benzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dried carbon disulfide solution (20 ml) of 2-ethyl-6-methoxy-benzofuran (2.76 g, 15.6 mmol) and p-anisoyl chloride (3.48 g, 20.3 mmol) was cooled on ice, to which tin chloride (IV) was dropped (5.25 g, 20.3 mmol) while stirring. The mixture was stirred at a temperature in a range of 5 to 10° C. for 3 hours and then poured into water. The organic layer was washed with diluted hydrochloric acid and water, dried over MgSO4, and concentrated under reduced pressure. Crude product thereof was purified by HPLC (silica gel, ethyl acetate: hexane=2:8) and a target product in pale yellow oily state (2.98 g, 9.60 mmol, 58%) was obtained.

Workup

  1. additionwas dropped (5.25 g, 20.3 mmol)
  2. stirringThe mixture was stirred at a temperature in a range of 5 to 10° C. for 3 hours
  3. washThe organic layer was washed with diluted hydrochloric acid and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customCrude product thereof was purified by HPLC (silica gel, ethyl acetate: hexane=2:8)
  7. customa target product in pale yellow oily state (2.98 g, 9.60 mmol, 58%) was obtained

Sources & evidence

ORD record
ord-578cc6e4b3fe4120b4865e6cc81a9820
Source dataset
uspto-grants-2009_04
Patent number
US07521570B2

Reaction notes

Loading…