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

HRID 19615

반응식

HRID 19615 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-99ee562778c24210ad8e6056e2283f5e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745446B2

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