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Water → 3-(5'-Nitro-2'-oxospiro[1,3-dioxane-2,3'-indol]-1'(2'H)-yl)propanenitrile

HRID 853887
ノート
印刷プレビュー

反応式

HRID 853887 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]12[O:18][CH2:17][CH2:16][CH2:15][O:14]1)([O-:3])=[O:2].[C:19](#[N:22])[CH:20]=[CH2:21].O>CN(C=O)C.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:21][CH2:20][C:19]#[N:22])[C:8](=[O:13])[C:7]12[O:18][CH2:17][CH2:16][CH2:15][O:14]1)([O-:3])=[O:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 962WaterHCID 7855AcrylonitrileHCID 337321165'-nitrospiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one

生成物 1

HCID 589325573-(5'-Nitro-2'-oxospiro[1,3-dioxane-2,3'-indol]-1'(2'H)-yl)propanenitrile収率 101.4%

試薬・触媒・溶媒 2

HCID 66854Benzyltrimethylammonium hydroxide触媒
HCID 6228
Dimethylformamide
溶媒

反応条件

温度
52 °C

実験手順

At room temperature, to a mixture of 5′-nitrospiro[1,3-dioxane-2,3′-indol]-2′(1′H)-one(1.75 g, 6.99 mmol) and benzyltrimethylammonium hydroxide (40% aqueous solution, 0.110 mL, 0.699 mmol, 0.1 mole %) in DMF (31 mL) was added acrylonitrile (0.921 mL, 14.0 mmol, 2 eq) drop-wise. and the mixture was heated at 52° C. for 2 hr. The reaction was cooled to room temperature and poured into H2O (160 mL). The reaction mixture was extracted with Et2O. The combined organic extracts were washed with brine and concentrated. The crude product was purified on Biotage KP silica gel eluting with 96/4 CH2Cl2/CH3CN to give the title compound as a yellow solid (2.15 g, 100% ). NMR (300 Mz, DMSO-d6): consistent

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThe reaction mixture was extracted with Et2O
  3. washThe combined organic extracts were washed with brine
  4. concentrationconcentrated
  5. customThe crude product was purified on Biotage KP silica gel eluting with 96/4 CH2Cl2/CH3CN

出典と根拠

ORDレコード
ord-13df433d10e34e2a9f912a95b69e9fa0
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07256198B2

反応ノート

読み込み中…

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