Dimethylformamide → Ethyl[(6,7-dichloro-2-acetylbenzo[b]thien-5-yl)oxy]acetate

HRID 370984ノート

反応式

HRID 370984 の反応式
[C:1]([C:4]1[S:8][C:7]2[C:9]([Cl:15])=[C:10]([Cl:14])[C:11]([OH:13])=[CH:12][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(=O)CC>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][O:13][C:11]1[C:10]([Cl:14])=[C:9]([Cl:15])[C:7]2[S:8][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][C:6]=2[CH:12]=1)[CH3:22]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 132900362-Acetyl-6,7-dichloro-5-hydroxybenzo[b]thiophene

生成物 1

HCID 53636860Ethyl[(6,7-dichloro-2-acetylbenzo[b]thien-5-yl)oxy]acetate収率 42.6%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒2 回

実験手順

To a solution of 9.0 g of 2-acetyl-6,7-dichloro-5-hydroxybenzo[b]thiophene and 200 ml of 2-butanone is added a solution of 6.62 g of ethyl bromoacetate in 50 ml of 2-butanone, 5.2 g of potassium carbonate and 2.2 ml of dimethylformamide. The reaction mixture is heated under reflux for 2 hrs, allowed to cool and filtered. The filtrate is extracted with ether (3 times). The layers are separated and the organic phase is washed with water, saturated sodium chloride solution, dried and filtered. The filtrate is evaporated. The residue is dissolved in dichloromethane and chromatographed on alumina, using dichloromethane as the eluant. Evaporation of the eluant gives 5.1 g of ethyl[(6,7-dichloro-2-acetylbenzo[b]thien-5-yl)oxy]acetate.

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 2 hrs
  3. temperatureto cool
  4. filtrationfiltered
  5. extractionThe filtrate is extracted with ether (3 times)
  6. customThe layers are separated
  7. washthe organic phase is washed with water, saturated sodium chloride solution
  8. customdried
  9. filtrationfiltered
  10. customThe filtrate is evaporated
  11. dissolutionThe residue is dissolved in dichloromethane
  12. customchromatographed on alumina
  13. customEvaporation of the eluant

出典と根拠

ORDレコード
ord-0bf20c0f6a074e1d873e012dd1a2c661
出典データセット
uspto-grants-1985_07
特許番号
US04528399

反応ノート

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