Hydrochloric Acid → 4-(4-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

HRID 512576ノート

反応式

HRID 512576 の反応式
C1(C)C=CC=CC=1.[CH3:8][C:9]1([CH3:19])[C:14](=[O:15])[CH2:13][C:12](=[O:16])[C:11]([CH3:18])([CH3:17])[O:10]1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:32][C:33]1[CH:38]=[CH:37][C:36]([Pb+3])=[C:35]([CH2:40][CH3:41])[CH:34]=1.Cl>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[Br:32][C:33]1[CH:38]=[CH:37][C:36]([CH:13]2[C:14](=[O:15])[C:9]([CH3:19])([CH3:8])[O:10][C:11]([CH3:18])([CH3:17])[C:12]2=[O:16])=[C:35]([CH2:40][CH3:41])[CH:34]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 199092752,2,6,6-Tetramethyloxane-3,5-dioneHCID 178476529HCID 178476529、化合物

生成物 1

HCID 497653874-(4-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

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

4-Dimethylaminopyridine (3.13 g, 25.7 mmol) and toluene (10 ml) are added to a solution of 2,2,6,6-tetramethylpyran-3,5-dione (0.87 g, 5.13 mmol) in chloroform (40 ml) and the reaction mixture is heated to 80° C. 4-Bromo-2-ethylphenyllead triacetate (3.50 g, 6.16 mmol) is added portionwise over 5 minutes, and once the addition is complete the reaction mixture is stirred at 80° C. for a further 4 hours. The mixture is cooled to room temperature, 2M aqueous hydrochloric acid (40 ml) is added, and the mixture is stirred vigorously for 20 minutes, then filtered through a small plug of diatomaceous earth, washing with dichloromethane (40 ml). The organic phase is separated, and the aqueous phase is extracted with dichloromethane (2×40 ml). The organic solutions are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-(4-bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione.

後処理

  1. additiononce the addition
  2. temperatureThe mixture is cooled to room temperature
  3. stirringthe mixture is stirred vigorously for 20 minutes
  4. filtrationfiltered through a small plug of diatomaceous earth
  5. washwashing with dichloromethane (40 ml)
  6. customThe organic phase is separated
  7. extractionthe aqueous phase is extracted with dichloromethane (2×40 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate is concentrated under reduced pressure
  11. customThe residue is purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-e5b3907b59f54e8594428494eda3d185
出典データセット
uspto-grants-2015_08
特許番号
US09102642B2

反応ノート

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