Toluene → 2-(5-Bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione

HRID 40479

반응식

HRID 40479 반응식
[C:1]1(=[O:7])[CH2:5][CH2:4][C:3](=[O:6])[CH2:2]1.C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:27][C:28]1[CH:29]=[CH:30][C:31]([CH:35]2[CH2:37][CH2:36]2)=[C:32]([Pb+3])[CH:33]=1>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl.ClCCl.Cl>[Br:27][C:28]1[CH:33]=[CH:32][C:31]([CH:35]2[CH2:37][CH2:36]2)=[C:30]([CH:2]2[C:3](=[O:6])[CH2:4][CH2:5][C:1]2=[O:7])[CH:29]=1

참가 물질

8

반응물 3

HCID 1140TolueneHCID 774661,3-CyclopentanedioneHCID 178419342HCID 178419342, 화합물

생성물 1

HCID 666768602-(5-Bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 313Hydrochloric Acid용매HCID 6212Chloroform용매HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

To a solution of cyclopentane-1,3-dione (0.57 g, 0.0058 mol) and 4-dimethylaminopyridine (3.64 g, 0.030 mol) in chloroform (33 ml) is added toluene (9 ml) then 5-bromo-2-cyclopropylphenyl lead triacetate (3.77 g, 0.0065 mol). This solution is heated at 80° C. for 20 hours then cooled to room temperature and diluted with dichloromethane and 2M aqueous hydrochloric acid. The resulting biphasic suspension is filtered through diatomaceous earth and the two phases are separated. The organic layer is further washed with 2M aqueous hydrochloric acid and the aqueous phase is extracted again with dichloromethane. All organic fractions are combined, washed with brine, dried over magnesium sulfate then concentrated in vacuo. The crude product is finally purified by flash column chromatography on silica gel (isohexane/ethyl acetate eluant) to afford 2-(5-bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione as a pale yellow solid.

후처리

  1. temperaturethen cooled to room temperature
  2. filtrationThe resulting biphasic suspension is filtered through diatomaceous earth
  3. customthe two phases are separated
  4. washThe organic layer is further washed with 2M aqueous hydrochloric acid
  5. extractionthe aqueous phase is extracted again with dichloromethane
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationthen concentrated in vacuo
  9. customThe crude product is finally purified by flash column chromatography on silica gel (isohexane/ethyl acetate eluant)

출처 및 근거

ORD 기록
ord-34572c46811e4ecc907e60bca4b397f0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530388B2

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