Oxalyl chloride → 6-Methoxy-1-benzothiophene-2,3-dione

HRID 1710466ノート

反応式

HRID 1710466 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[C:10](Cl)(=[O:14])[C:11](Cl)=[O:12].[Cl-].[Al+3].[Cl-].[Cl-]>CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:10](=[O:14])[C:11](=[O:12])[S:9][C:5]=2[CH:4]=1

参加物

5

反応物 3

HCID 65578Oxalyl chlorideHCID 849893-MethoxybenzenethiolHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 34408486-Methoxy-1-benzothiophene-2,3-dione収率 47.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a solution of 3-methoxythiophenol (3.75 g, 26.7 mmol) in ether (20 mL) was added oxalyl chloride (3.7 mL, 43 mmol) dropwise. The mixture was heated at reflux for 1.5 h, cooled to rt, and concentrated in vacuo. The resulting yellow oil was dissolved in dichloromethane (50 mL), cooled to 0° C., and was treated with aluminum chloride (4.30 g, 32.0 mmol) in portions. The mixture was heated at reflux for 30 min, cooled to rt, and poured onto ice water with stirring. The organic layer was separated and successively washed with saturated, aqueous sodium bicarbonate, water, and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (4/1 ethyl acetate/hexane) which provided 2.46 g (47%) of 6-methoxy-1-benzothiophene-2,3-dione as an orange solid.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1.5 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting yellow oil was dissolved in dichloromethane (50 mL)
  5. temperaturecooled to 0° C.
  6. temperatureThe mixture was heated
  7. temperatureat reflux for 30 min
  8. temperaturecooled to rt
  9. additionpoured onto ice water
  10. customThe organic layer was separated
  11. washsuccessively washed with saturated, aqueous sodium bicarbonate, water, and brine
  12. dry with materialThe organic layer was dried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo
  15. customThe residue was purified by chromatography (4/1 ethyl acetate/hexane) which

出典と根拠

ORDレコード
ord-ea84e6025bfc44869b4bb1eac1393b9c
出典データセット
uspto-grants-2010_09
特許番号
US07790722B2

反応ノート

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