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

HRID 40479

反応式

HRID 40479 の反応式
[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

参加物

8

反応物 3

HCID 1140TolueneHCID 774661,3-CyclopentanedioneHCID 178419342HCID 178419342、化合物

生成物 1

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

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 313Hydrochloric Acid溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-34572c46811e4ecc907e60bca4b397f0
出典データセット
uspto-grants-2013_09
特許番号
US08530388B2

関連ノート

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