Diethyl Ether → 2-(4-Chlorophenyl)-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone

HRID 635362노트

반응식

HRID 635362 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:13]#N)[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([CH2:20][Mg]Cl)=[CH:18][CH:17]=1.ClC1C=CC(CCl)=CC=1.[Mg].CC[O:37]CC>C1(C)C=CC=CC=1>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([CH2:20][C:13]([C:9]2([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH2:12][CH2:11][CH2:10]2)=[O:37])=[CH:18][CH:17]=1

참가 물질

7

반응물 5

HCID 3283Diethyl EtherHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 5462224MagnesiumHCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrileHCID 178478997HCID 178478997, 화합물

생성물 1

HCID 212584342-(4-Chlorophenyl)-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 1-(3,4-dichlorophenyl)cyclobutanecarbonitrile (6.56 g) in toluene (100 ml) was added dropwise under nitrogen to a stirred solution of 4-chlorobenzylmagnesium chloride [prepared in the usual manner from 4-chlorobenzyl chloride (9.07) and magnesium (1.08 g)] in ether (100 ml). When the addition was complete, ether was distilled from the mixture until the internal temperature rose to 95° C., then the mixture was stirred at this temperature for 19 h, cooled to ambient temperature, and quenched by the dropwise addition of water (50 ml) followed by concentrated hydrochloric acid (10 ml). The mixture was stirred at 95° C. for 3 hours, then it was cooled to ambient temperature. The organic phase was separated, washed with water (100 ml) and saturated brine (100 ml), dried (Na2SO4), and the solvent was removed in vacuo. The residue was purified via flash chromatography over silica using 1:9-1:4 mixtures of ethyl acetate and petroleum ether (b.p. 60-80° C.) as eluant. Appropriate fractions were combined and the solvents removed in vacuo to give 2-(4-chlorophenyl)-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone as a yellow oil (7.51 g) which solidified slowly at ambient temperature to give a yellow solid, m.p. 82-84° C.

후처리

  1. additionWhen the addition
  2. distillationether was distilled from the mixture until the internal temperature
  3. customrose to 95° C.
  4. customquenched by the dropwise addition of water (50 ml)
  5. stirringThe mixture was stirred at 95° C. for 3 hours
  6. temperatureit was cooled to ambient temperature
  7. customThe organic phase was separated
  8. washwashed with water (100 ml) and saturated brine (100 ml)
  9. dry with materialdried (Na2SO4)
  10. customthe solvent was removed in vacuo
  11. customThe residue was purified via flash chromatography over silica using 1:9-1:4 mixtures of ethyl acetate and petroleum ether (b.p. 60-80° C.) as eluant
  12. customthe solvents removed in vacuo

출처 및 근거

ORD 기록
ord-7f22ec8ef15846909fa73dff761cc1ed
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187802B1

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