Benzene → HCID 68473849, compound

HRID 42679Notes

Reaction equation

HRID 42679 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[S:9][C:10]([CH3:24])=[CH:11][C:12]=1[C:13](=O)[C:14]([C:16]1[CH:20]=[C:19]([CH3:21])[S:18][C:17]=1[CH3:22])=O.[CH:25]1[CH:30]=CC=[CH:27][CH:26]=1>>[CH3:7][C:8]1[S:9][C:10]([CH3:24])=[CH:11][C:12]=1[C:13]1[CH:30]=[CH:25][CH2:26][CH2:27][C:14]=1[C:16]1[CH:20]=[C:19]([CH3:21])[S:18][C:17]=1[CH3:22]

Participants

4

Reactant 3

HCID 241Benzene2×HCID 114259331,2-Bis(2,5-dimethylthiophen-3-yl)ethane-1,2-dioneHCID 23665647Potassium tert-butoxide

Product 1

HCID 68473849HCID 68473849, compoundYield 25%

Procedure

Potassium t-butoxide (163 mg, 1.45 mmol) was added to a suspension of 1,4-butanebis(triphenylphosphonium)dibromide (537 mg, 0.725 mmol) in benzene (50 mL). The reaction was stirred for 45 min at room temperature. The resulting orange solution was heated to reflux and treated drop-wise with a solution of 1,2-bis(2,5-dimethyl-3-thienyl)ethanedione 23 (202 mg, 0.72 mmol) in benzene (25 mL). The reaction mixture was stirred at reflux for 20 min, at which point the heating mantle was removed and the reaction was allowed to cool to room temperature. The reaction was quenched by the addition of water (50 mL) and extracted with Et2O (3×50 mL). The organic extracts were combined, washed with brine, dried over MgSO4 and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography through silica (1:9 EtOAc:hexanes) to yield 55 mg (25%) of 25 as a white solid. Mp=55-57° C. 1H NMR (CDCl3): δ=6.13 (s, 2H), 5.88 (m, 2H), 2.26 (m, 10H), 2.14 (s, 6H); 13C NMR (CDCl3) δ=137.8, 134.4, 133.9, 131.6, 127.4, 126.7, 22.7, 15.1, 14.0. MS (EI): m/z=300 (M+).

Workup

  1. temperatureThe resulting orange solution was heated
  2. temperatureto reflux
  3. stirringThe reaction mixture was stirred
  4. temperatureat reflux for 20 min, at which point the heating mantle
  5. customwas removed
  6. temperatureto cool to room temperature
  7. customThe reaction was quenched by the addition of water (50 mL)
  8. extractionextracted with Et2O (3×50 mL)
  9. washwashed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customThe solvent was removed under reduced pressure
  13. customthe residue was purified by column chromatography through silica (1:9 EtOAc:hexanes)

Sources & evidence

ORD record
ord-f246ee6445da40f285820435dc765a45
Source dataset
uspto-grants-2013_09
Patent number
US08536205B2

Reaction notes

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