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Dimethylformamide → 3-Methoxycarbonylvinylcarbazole

HRID 448515
ノート
印刷プレビュー

反応式

HRID 448515 の反応式
CN(C=O)C.I[C:7]1[CH:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3.C(N(CCCC)CCCC)CCC.[C:33]([O:37][CH3:38])(=[O:36])[CH:34]=[CH2:35]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:38][O:37][C:33]([CH:34]=[CH:35][C:7]1[CH:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:36]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 7294Methyl AcrylateHCID 7622TributylamineHCID 36780693-iodo-9H-carbazole2 回

生成物 1

HCID 668960893-Methoxycarbonylvinylcarbazole収率 62%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate
触媒
HCID 962Water溶媒

実験手順

To a DMF solution (0.25 mL) of palladium acetate (38.0 mg, 0.17 μmol), compound (1) (0.50 g, 1.71 mmol) as well as tributylamine (0.41 μL, 1.71 mmol), methyl acrylate (0.38 L, 4.27 mmol) and H2O (1.0 mL) were added in this order. The reaction solution was allowed to react for 10 minutes at 160° C. using microwaves, and the reaction was traced by TLC to confirm the disappearance of compound (1). The palladium powder was removed by Kiriyama filtration, and then the residue was purified by column chromatography (HexH:AcOEt=3:1). Thus, compound (7) (0.26 g, 62%) was obtained as a white powder.

後処理

  1. customto react for 10 minutes at 160° C.
  2. customThe palladium powder was removed by Kiriyama filtration
  3. customthe residue was purified by column chromatography (HexH:AcOEt=3:1)

出典と根拠

ORDレコード
ord-570aca7291c54e3395455cea8e0bcd9f
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08481714B2

反応ノート

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