Water → 2,4-Dichlorophenyl 1-(3-pyridyl)-cyclopropyl ketone

HRID 1087403ノート

反応式

HRID 1087403 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:17])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[I-].Cl[CH2:20][CH2:21][S+](C)C.[I-].[Na+].O>C(O)(C)(C)C>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:10]2([C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[O:17])[CH2:21][CH2:20]2)[CH:12]=1

参加物

6

反応物 4

HCID 962WaterHCID 5238Sodium IodideHCID 10912030(2-Chloroethyl)diMethylsulfoniuM iodideHCID 13488634Ethanone, 1-(2,4-dichlorophenyl)-2-(3-pyridinyl)-

生成物 1

HCID 198170702,4-Dichlorophenyl 1-(3-pyridyl)-cyclopropyl ketone収率 70.3%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
45 °C

実験手順

54 g of 2',4'-dichloro-2-(3-pyridyl)-acetophenone are added portionwise under an inert gas to a suspension of 46.5 g of freshly sublimed potassium tert.butylate in 590 ml of tert.butanol and the reaction mixture is stirred at 45° C. for 2 hours. The mixture is treated at room temperature with 59.5 g of 2-chloroethyl-dimethylsulphonium iodide and a spatula tip of sodium iodide and the mixture is held at 50° C. for 16 hours while stirring vigorously. The mixture is poured into water and extracted three times with 300 ml of diethyl ether each time. The combined organic extracts are washed with water, dried over anhydrous sodium sulphate and evaporated under reduced pressure. The residue is chromatographed on silica gel with diethyl ether as the eluent and crystallized from diethyl ether/n-hexane. There are obtained 41.7 g of 2,4-dichlorophenyl 1-(3-pyridyl)-cyclopropyl ketone as white crystals, m.p. 83° C.

後処理

  1. stirringwhile stirring vigorously
  2. extractionextracted three times with 300 ml of diethyl ether each time
  3. washThe combined organic extracts are washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel with diethyl ether as the eluent
  7. customcrystallized from diethyl ether/n-hexane

出典と根拠

ORDレコード
ord-241d5b1d37f44a91bc2301947303c2fb
出典データセット
uspto-grants-1991_07
特許番号
US05036074

反応ノート

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