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

HRID 1506661ノート

反応式

HRID 1506661 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-87a12a81f3ff4951aaca26b829b1799c
出典データセット
uspto-grants-2015_12
特許番号
US09220710B2

反応ノート

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