Aluminium lithium hydride → HCID 178519842、化合物

HRID 2368476ノート

反応式

HRID 2368476 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13](N(OC)C)=[O:14])=[CH:11][N:10]=[C:9]2[SH:19])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:13]=[O:14])=[CH:11][N:10]=[C:9]2[SH:19])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 178502684HCID 178502684、化合物

生成物 1

HCID 178519842HCID 178519842、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1-(4-fluorophenyl)-2-mercapto-N-methoxy-N-methyl-1H-imidazole-5-carboxamide (8) (1 g, 3.55 mmol) in anhydrous THF (71 mL) at 0° C. was added lithium aluminum hydride (2M in THF, 5.3 mL, 10.65 mmol). The reaction was stirred at 0° C. for 1 h and for an additional 3 h at room temperature. The reaction was quenched at 0° C. with 15% sodium bicarbonate (40 mL) and water (40 mL) and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes) to afford 1-(4-fluorophenyl)-2-mercapto-1H-imidazole-5-carbaldehyde (12).

後処理

  1. customThe reaction was quenched at 0° C. with 15% sodium bicarbonate (40 mL) and water (40 mL)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-88884bbf4a0d4d2080cdae6e6ad65096
出典データセット
uspto-grants-2014_04
特許番号
US08703776B2

反応ノート

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