1-tosyl-3-acetylpyrrole → 2-Chloro-1-[1-(4-methylbenzene-1-sulfonyl)-1H-pyrrol-3-yl]ethan-1-one

HRID 345951ノート

反応式

HRID 345951 の反応式
[Cl-].[Ca+2].[Cl-].[C:4]([C:7]1[CH:11]=[CH:10][N:9]([S:12]([C:15]2[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:8]=1)(=[O:6])[CH3:5].[Cl:22]C(=C(Cl)C(Cl)=C(Cl)C(Cl)Cl)C=O>CO>[Cl:22][CH2:5][C:4]([C:7]1[CH:11]=[CH:10][N:9]([S:12]([C:15]2[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:8]=1)=[O:6]

参加物

5

反応物 3

HCID 27377871-tosyl-3-acetylpyrroleHCID 5284359Calcium ChlorideHCID 54378597HCID 54378597、化合物

生成物 1

HCID 151807422-Chloro-1-[1-(4-methylbenzene-1-sulfonyl)-1H-pyrrol-3-yl]ethan-1-one収率 53%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

In a 100 cm3 one neck flask fitted with a condenser and a calcium chloride guard, 4 g of 3-acetyl-1-tosyl pyrrole 2 (15 mmoles) was introduced together with 30 cm3 of methanol. Then 4.5 g of 2,3,4,5,6,6-hexachloro-2,4-hexadiene-1-one (15 mmoles) was set under reflux during 6 hours and maintained under stirring at ambient temperature during one night. The solvent was evaporated and the crude product (8.5 g) was dissolved in 15 cm3 of chloroform, filtered (the pentachlorophenol was not very soluble in this solvent) and separated on silica gel column (250 g; 60-200 82 m; eluting with 1-29-70 acetic acid-ethyl acetate-heptane; VR =650 cm3) to give 2.35 g of white crystals 3 (M=297.5, yield: 53%).

後処理

  1. temperatureunder reflux during 6 hours
  2. temperaturemaintained
  3. customThe solvent was evaporated
  4. dissolutionthe crude product (8.5 g) was dissolved in 15 cm3 of chloroform
  5. filtrationfiltered (the pentachlorophenol
  6. customseparated on silica gel column (250 g; 60-200 82 m; eluting with 1-29-70 acetic acid-ethyl acetate-heptane; VR =650 cm3)

出典と根拠

ORDレコード
ord-8857202108304af09e4bcc89786b322e
出典データセット
uspto-grants-1991_10
特許番号
US05059694

反応ノート

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