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Bromopinacolone → 2-(3,3-dimethyl-2-oxobutyl)-1H-isoindole-1,3(2H)-dione

HRID 1870084
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HRID 1870084 반응식
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]>C1(C)C=CC=CC=1>[CH3:17][C:16]([CH3:19])([CH3:18])[C:15](=[O:20])[CH2:14][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]
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참가 물질

4

반응물 2

HCID 21642BromopinacoloneHCID 24194345Phthalimide potassium salt

생성물 1

HCID 3043232-(3,3-dimethyl-2-oxobutyl)-1H-isoindole-1,3(2H)-dione수율 76.2%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Potassium phthalimide (82.86 g, 0.447 mol) is added to a stirred solution of bromopinacolone (80.10 g, 0.447 mol) in toluene (300 ml). The-suspension is refluxed for 19 h, cooled, and then the precipitate is filtered off and discarded. The filtrate is cooled in an ice-bath and treated with petroleum ether (550 ml). The resulting precipitate is collected by filtration. The mother liquor is reduced to circa 100 ml by evaporation in vacuo, and a further quantity of precipitate which forms is collected by filtration and combined with the first crop, giving 2-(3,3-dimethyl-2-oxo-butyl)-isoindole-1,3-dione (total yield 83.5 g, 76%) as colourless crystals, m.p. 96-99° C.

후처리

  1. temperatureThe-suspension is refluxed for 19 h
  2. temperaturecooled
  3. filtrationthe precipitate is filtered off
  4. temperatureThe filtrate is cooled in an ice-bath
  5. additiontreated with petroleum ether (550 ml)
  6. filtrationThe resulting precipitate is collected by filtration
  7. customThe mother liquor is reduced to circa 100 ml by evaporation in vacuo
  8. filtrationa further quantity of precipitate which forms is collected by filtration

출처 및 근거

ORD 기록
ord-bd5e522a2f604026ab60fef54411968d
출처 데이터셋
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06096688

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