Benzene → HCID 68473849、化合物

HRID 42679ノート

反応式

HRID 42679 の反応式
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]

参加物

4

反応物 3

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

生成物 1

HCID 68473849HCID 68473849、化合物収率 25%

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-f246ee6445da40f285820435dc765a45
出典データセット
uspto-grants-2013_09
特許番号
US08536205B2

反応ノート

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