Diisobutylaluminum hydride → 5-(4-Chlorophenyl)oxazole-4-carbaldehyde

HRID 1506661노트

반응식

HRID 1506661 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][CH:11]=[N:10][C:9]=2[C:13](OCC)=[O:14])=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][CH:11]=[N:10][C:9]=2[CH:13]=[O:14])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 2739479Ethyl 5-(4-chlorophenyl)oxazole-4-carboxylate

생성물 1

HCID 153155355-(4-Chlorophenyl)oxazole-4-carbaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-20 °C

실험 절차

To a solution of 33C (1.25 g, 5 mmol) in THF was added DIBAL-H (1.0 M in toluene, 10 mmol) dropwise at −70° C. The resulting solution was allowed to warm to −20° C. over 3 h. Upon completion of the reaction, saturated aqueous NH4Cl was added to the flask and the mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was used in the next step without further purification. MS (m/z) 208.1 [M+H]+.

후처리

  1. additionwas added to the flask
  2. customthe mixture was partitioned between EtOAc and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was used in the next step without further purification

출처 및 근거

ORD 기록
ord-87a12a81f3ff4951aaca26b829b1799c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09220710B2

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