ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Methanol → (E)-3-[7-Hydroxy-6-methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzofuran-2-yl]-acrylic acid methyl ester

HRID 218834
ノート
印刷プレビュー

反応式

HRID 218834 の反応式
Br[C:2]1[O:3][C:4]2[C:24]([O:25]C(=O)C)=[C:23]([O:29][CH3:30])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1.[CH3:31][O:32][C:33](=[O:36])[CH:34]=[CH2:35].CO.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:31][O:32][C:33](=[O:36])/[CH:34]=[CH:35]/[C:2]1[O:3][C:4]2[C:24]([OH:25])=[C:23]([O:29][CH3:30])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:9]=[C:10]([O:18][CH3:19])[C:11]([O:16][CH3:17])=[C:12]([O:14][CH3:15])[CH:13]=1
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 887MethanolHCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 247865602-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

生成物 1

HCID 24786669(E)-3-[7-Hydroxy-6-methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzofuran-2-yl]-acrylic acid methyl ester収率 37%

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 6342Acetonitrile溶媒

実験手順

Mixture of 2-bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuran (50 mg, 0.10 mmol) and methylacrylate (0.5 mL, excess) in a mixture of acetonitrile: TEA; 1 mL:0.5 mL was degassed with nitrogen and palladium acetate (10 mg) was added to it. Reaction mixture was stirred for one hour under nitrogen at reflux, more palladium acetate (15 mg) was added and the refluxing was continued for 7 hours (monitored by tlc). Methanol (1 mL) was added followed by the addition of potassium carbonate (70 mg, 0.51 mmol) and stirring was continued for 1 hour. Solvent was distilled and the crude material was purified over silica gel column (eluent Hexane:diethylether; 1:1) to afford the title compound as yellow crystalline solid (17 mg, 37%); 1H NMR (300 MHz, CDCl3) δ 7.61(d, 1H, J=15.76 Hz), 7.14(s, 2H, benzoyl Hs), 6.98(d, 1H, J=8.64 Hz), 6.89(d, 1H, J=8.69 Hz), 6.81(d, 1H, J=15.78 Hz), 3.96(s, 3H, OMe), 3.95(s, 3H, OMe), 3.81(s, 6H, 2×OMe), 3.77(bs, 3H, OMe).

後処理

  1. custom1 mL:0.5 mL was degassed with nitrogen and palladium acetate (10 mg)
  2. additionwas added to it
  3. customReaction mixture
  4. temperatureat reflux
  5. waitthe refluxing was continued for 7 hours
  6. stirringstirring
  7. waitwas continued for 1 hour
  8. distillationSolvent was distilled
  9. customthe crude material was purified over silica gel column (eluent Hexane:diethylether; 1:1)

出典と根拠

ORDレコード
ord-08d4daf1d9d3408bb3513647d4808e95
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08198466B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート