Tin tetrachloride → 1,2-Di-2-thienylethanone

HRID 2372367Notes

Reaction equation

HRID 2372367 reaction equation
Cl[Sn](Cl)(Cl)Cl.[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH2:11][C:12](Cl)=[O:13]>C(Cl)Cl>[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:12](=[O:13])[CH2:11][C:7]1[S:6][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24287Tin tetrachlorideHCID 1623622-Thiopheneacetyl chloride

Product 1

HCID 134271651,2-Di-2-thienylethanoneYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

SnCl4 (1.01 g, 3.94 mmol) in CH2Cl2 (5 ml) was added to 2-thiophenylacetyl chloride (6.33 g, 39.4 mmol) and thiopene (3.32 g, 39.4 mmol) in CH2Cl2 (300 ml) at room temperature. The reaction was complete (by TLC) after 3 hours. The solution was poured over a 10% aqueous HCl/ice slurry. The organic layer was separated, washed twice with H2O and dried over MgSO4. The solvent was removed under reduced pressure. The crude oil was chromatographed on SiO2 (300 g), eluting with Hexane/CH2Cl2, 1/1 to afford 30 (3.3 g, 40.5%).

Workup

  1. customat room temperature
  2. customafter 3 hours
  3. customThe organic layer was separated
  4. washwashed twice with H2O
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed under reduced pressure
  7. customThe crude oil was chromatographed on SiO2 (300 g)
  8. washeluting with Hexane/CH2Cl2, 1/1

Sources & evidence

ORD record
ord-09b93bd6907c4081bd45590562a9a4a3
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

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