Trifluoroacetic acid → HCID 46914013、化合物

HRID 597846ノート

反応式

HRID 597846 の反応式
FC(F)(F)[C:3](O)=[O:4].[CH2:8]([O:10][C:11](=[O:24])[CH2:12][CH2:13][C:14]1[C:22]2[C:21](=[O:23])[CH2:20][CH2:19][CH2:18][C:17]=2[NH:16][CH:15]=1)[CH3:9].COC(OC)OC.[OH-].[Na+]>O.C(OCC)(=O)C>[CH2:8]([O:10][C:11](=[O:24])[CH2:12][CH2:13][C:14]1[C:22]2[C:21](=[O:23])[CH2:20][CH2:19][CH2:18][C:17]=2[NH:16][C:15]=1[CH:3]=[O:4])[CH3:9]

参加物

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 9005Trimethyl orthoformateHCID 14798Sodium HydroxideHCID 46914009HCID 46914009、化合物

生成物 1

HCID 46914013HCID 46914013、化合物収率 19%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a trifluoroacetic acid solution (47 mL) containing 3-(3-ethoxy-3-oxopropyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole (4, 10.0 g, 42.5 mmol) was added with trimethylorthoformate (13.6 g, 128 mmol) at 0° C. The reaction was stirred at 0° C. for 30 min, warmed up to room temperature and stirred for 2.0 h. The solution was added with ethyl acetate (250 mL), water (200 mL) and NaOH (18 g). The organic layer was collected and washed with saturated aqueous NaHCO3 (200 mL), dried over MgSO4 (s), and concentrated under reduced pressure. The oily residue was purified by gravity column chromatography (50% EtOAc in hexanes) to give 3-(3-ethoxy-3-oxopropyl)-2-formyl-4-oxo-4,5,6,7-tetrahydro-1H-indole (5, 2.1 g, 8.0 mmol) as yellow solids in 19% yield.

後処理

  1. temperaturewarmed up to room temperature
  2. stirringstirred for 2.0 h
  3. customThe organic layer was collected
  4. washwashed with saturated aqueous NaHCO3 (200 mL)
  5. dry with materialdried over MgSO4 (s)
  6. concentrationconcentrated under reduced pressure
  7. customThe oily residue was purified by gravity column chromatography (50% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-9e917815dc6a42dea3435fc387666331
出典データセット
uspto-grants-2011_03
特許番号
US07897602B2

反応ノート

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