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

HRID 1087403노트

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HRID 1087403 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6386tert-Butanol용매

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온도
45 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-241d5b1d37f44a91bc2301947303c2fb
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05036074

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