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Potassium Carbonate → (Z)-9-((1,3-dioxoisoindolin-2-yl)methyl)-2,5-dihydrobenzo[b][1,4]dioxocine-8-carbonitrile

HRID 1186034
ノート
印刷プレビュー

反応式

HRID 1186034 の反応式
Cl[CH2:2]/[CH:3]=[CH:4]\[CH2:5]Cl.[O:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[N:9]1[CH2:18][C:19]1[CH:26]=[C:25]([OH:27])[C:24]([OH:28])=[CH:23][C:20]=1[C:21]#[N:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:17]=[C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](=[O:7])[N:9]1[CH2:18][C:19]1[C:20]([C:21]#[N:22])=[CH:23][C:24]2[O:28][CH2:5][CH:4]=[CH:3][CH2:2][O:27][C:25]=2[CH:26]=1
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

5

反応物 3

HCID 11430Potassium CarbonateHCID 64321151,4-Dichloro-cis-2-buteneHCID 582456992-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5-dihydroxy-benzonitrile

生成物 1

HCID 58245715(Z)-9-((1,3-dioxoisoindolin-2-yl)methyl)-2,5-dihydrobenzo[b][1,4]dioxocine-8-carbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

cis-1,4-Dichloro-2-butene (0.200 g, 1.6 mmol), 2((1,3-dioxoisoindolin-2-yl)methyl)-4,5-dihydroxybenzonitrile (0.500 g, 1.7 mmol), and potassium carbonate (0.77 g, 5.6 mmol) were suspended in dry DMF (80 ml) and heated to 50° C. for 5 h. The resulting mixture was cooled to room temperature and stirred overnight, then filtered. The filtrate was diluted with ethyl acetate, washed with water (2×), brine (2×), dried (Na2SO4) and concentrated in vacuo. The resulting residue was chromatographed eluting with ethyl acetate/heptanes (50:50) to yield (Z)-9-((1,3-dioxoisoindolin-2-yl)methyl)-2,5-dihydrobenzo[b][1,4]dioxocine-8-carbonitrile as a residue. 1H NMR (CDCl3): δ 7.94-7.86 (m, 2H), 7.78-7.73 (m, 2H), 7.32 (s, 1H), 6.83 (s, 1H), 5.92-5.85 (m, 2H), 4.98 (s, 4H), 4.80 (s, 2H).

後処理

  1. temperatureThe resulting mixture was cooled to room temperature
  2. filtrationfiltered
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with water (2×), brine (2×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was chromatographed
  8. washeluting with ethyl acetate/heptanes (50:50)

出典と根拠

ORDレコード
ord-b65fedcadacf4917979dffc016930505
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08673890B2

反応ノート

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