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Potassium Iodide → HCID 57426205、化合物

HRID 551047
ノート
印刷プレビュー

反応式

HRID 551047 の反応式
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:7][NH:8]2)([O-:3])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>CC(C)=O>[C:34]([O:33][C:31](=[O:32])[CH2:30][N:8]1[C:9]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=2)[CH:6]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:7]1)([CH3:37])([CH3:36])[CH3:35]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 79177tert-Butyl bromoacetateHCID 57426204HCID 57426204、化合物

生成物 1

HCID 57426205HCID 57426205、化合物

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of ethyl 4-(4-nitro-2,3-dihydro-1H-indol-3-yl)butanoate from Step B (1.10 g, 3.95 mmol), sodium carbonate (628 mg, 5.93 mmol), and potassium iodide (131 mg, 0.79 mmol) in acetone (10 mL) was added tert-butyl bromoacetate (17.5 mL, 119 mmol). The mixture was heated at reflux for 18 h, then cooled to ambient temperature and concentrated in vacuo. The residue was partitioned between H2O (30 mL) and EtOAc (2×60 mL) and the organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—90:10 to 65:35, to give the title compound. MS: m/z=365 (M+1).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between H2O (30 mL) and EtOAc (2×60 mL)
  5. dry with materialthe organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of hexane

出典と根拠

ORDレコード
ord-e82dd178f4484755937cde8c839fbff3
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07947677B2

反応ノート

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