Ammonium Chloride → (E)-1-(3-Bromo-phenyl)-5-methoxy-pent-4-ene-1,3-dione

HRID 19615

反応式

HRID 19615 の反応式
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:11][O:12][CH:13]=[CH:14][C:15](=[O:17])[CH3:16].[Br:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](Cl)=[O:23].[Cl-].[NH4+]>C1COCC1>[Br:18][C:19]1[CH:20]=[C:21]([C:22](=[O:23])[CH2:16][C:15](=[O:17])/[CH:14]=[CH:13]/[O:12][CH3:11])[CH:25]=[CH:26][CH:27]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 74377Benzoyl chloride, 3-bromo-HCID 942973-Buten-2-one, 4-methoxy-HCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 67318718(E)-1-(3-Bromo-phenyl)-5-methoxy-pent-4-ene-1,3-dione

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

In a 1 ltr flask is cooled a solution of lithium hexamethyldisilazide (65 ml, 1.5 M) in THF (250 ml) to 75 ° C. During a period of 1 h is added 4-methoxy-but-3-en-2-one (7 ml). The mixture is stirred for 1 h at −70° C. A solution of 3-bromobenzoylchloride (6 g) in THF (250 ml) is added to the above mixture during 1 h at −70° C. The resulting mixture is slowly heated to ambient temperature and stirred for 1 h. Subsequently, the mixture is added to a cold aqueous solution of ammonium chloride and the resulting suspension is extracted with ethyl acetate. The organic phase is extracted twice with an aqueous solution of ammonium chloride, dried over sodium sulfate and evaporated. The crude oily product is transferred to the next step without any further purification.

後処理

  1. temperatureThe resulting mixture is slowly heated to ambient temperature
  2. stirringstirred for 1 h
  3. extractionthe resulting suspension is extracted with ethyl acetate
  4. extractionThe organic phase is extracted twice with an aqueous solution of ammonium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe crude oily product is transferred to the next step without any further purification

出典と根拠

ORDレコード
ord-99ee562778c24210ad8e6056e2283f5e
出典データセット
uspto-grants-2010_06
特許番号
US07745446B2

関連ノート

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