Hydrochloric Acid → HCID 49765293、化合物

HRID 537670ノート

反応式

HRID 537670 の反応式
C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:21][CH3:22])=[C:18]([Pb+3])[CH:19]=1.[C:23]1(=[O:30])[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH2:24]1.C1(C)C=CC=CC=1.Cl>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:21][CH3:22])=[C:18]([CH:24]2[C:25](=[O:29])[CH2:26][CH2:27][CH2:28][C:23]2=[O:30])[CH:19]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 104341,3-CyclohexanedioneHCID 178476533HCID 178476533、化合物

生成物 1

HCID 49765293HCID 49765293、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6212Chloroform溶媒

反応条件

温度
80 °C

実験手順

To a solution of 5-bromo-2-ethylphenyllead triacetate (20.00 g, 35.2 mmol) (described in WO08/071,405) in chloroform (100 ml) is added cyclohexane-1,3-dione (3.94 g, 35.2 mmol) and 4-dimethylaminopyridine (22.36 g, 176 mmol). After stirring the reaction at room temperature for 5 minutes toluene (50 ml) is added and the solution is heated at 80° C. for 4 hours. After cooling to room temperature the mixture is allowed to stand overnight, followed by treatment with 2M aqueous hydrochloric acid. Following filtration of the precipitate the biphasic solution is separated, and the aqueous phase is extracted again with dichloromethane (×2). Organic fractions are combined then evaporated under reduced pressure to yield a crude product which is purified by flash column chromatography (10% ethyl acetate/hexane to 70% ethyl acetate/hexane eluant) to afford 2-(5-bromo-2-ethylphenyl)cyclohexane-1,3-dione as a white solid.

後処理

  1. additionis added
  2. temperatureAfter cooling to room temperature the mixture
  3. filtrationfiltration of the precipitate the biphasic solution
  4. customis separated
  5. extractionthe aqueous phase is extracted again with dichloromethane (×2)
  6. customOrganic fractions are combined then evaporated under reduced pressure
  7. customto yield a crude product which
  8. customis purified by flash column chromatography (10% ethyl acetate/hexane to 70% ethyl acetate/hexane eluant)

出典と根拠

ORDレコード
ord-7d68571fb2e24128991a89d0db4d2ca2
出典データセット
uspto-grants-2014_10
特許番号
US08865623B2

反応ノート

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