4-Chlorophenyl cyclopropyl ketone → 1-[1-(p-Chlorophenyl)-2-methoxyvinyl]cyclopropane

HRID 610855

반응식

HRID 610855 반응식
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH:29]1([C:32]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)=O)[CH2:31][CH2:30]1>CCOCC>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([C:32]([CH:29]2[CH2:31][CH2:30]2)=[CH:2][O:3][CH3:4])=[CH:35][CH:36]=1

참가 물질

5

반응물 3

HCID 811484-Chlorophenyl cyclopropyl ketoneHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 178418339Butyllithium

생성물 1

HCID 539422601-[1-(p-Chlorophenyl)-2-methoxyvinyl]cyclopropane수율 60%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
2.5 °C

실험 절차

A solution of methoxymethyl triphenyl phosphonium chloride (20.5 g, 0.060 mol) in ether is cooled to -60° C., treated with a 2.5M solution of butyllithium in hexanes (25.2 mL, 0.063 mol), warmed to and stirred at 0-5° C. for 90 minutes, recooled to -60° C., treated with a solution of 4-chlorophenyl cyclopropyl ketone (9.03 g, 0.050 mol) in ether, warmed to and stirred at room temperature overnight, quenched with ethyl acetate and 2N hydrochloric acid, and extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water, 2N hydrochloric acid and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and an ethyl acetate/hexanes solution (1:9) gives the title product as an oil (6.2 g, 60%).

후처리

  1. temperaturewarmed to and
  2. customrecooled to -60° C.
  3. temperaturewarmed to and
  4. stirringstirred at room temperature overnight
  5. customquenched with ethyl acetate and 2N hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. washwashed sequentially with water, 2N hydrochloric acid and water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customto obtain a residue

출처 및 근거

ORD 기록
ord-eee5c3742f254ec3b383a988b5b6bc1f
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998673

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