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1,1,3,3-Tetramethylguanidine → (z)-2-Ethoxy-3-(1h-indol-4-yl)-acrylic acid ethyl ester

HRID 11380
ノート
印刷プレビュー

反応式

HRID 11380 の反応式
[Cl-].[CH2:2]([O:4][CH:5]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:3].CN(C)C(=N)N(C)C.[CH:38]([C:40]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:41]=1[CH:42]=[CH:43][NH:44]2)=O>ClCCl>[CH2:9]([O:8][C:6](=[O:7])/[C:5](/[O:4][CH2:2][CH3:3])=[CH:38]/[C:40]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:41]=1[CH:42]=[CH:43][NH:44]2)[CH3:10]
参加物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 664601,1,3,3-Tetramethylguanidine2 回HCID 333703Indole-4-carboxaldehydeHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)

生成物 1

HCID 69280560(z)-2-Ethoxy-3-(1h-indol-4-yl)-acrylic acid ethyl ester収率 107.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 35.01 g (81.6 mmol) of (1,2-diethoxy-2-oxoethyl)triphenyl phosphonium chloride in 200 ml of dichloromethane was added at 0° C. 11.01 ml (87.1 mmol) of tetramethyl guanidine and the mixture was warmed to 22° C. The mixture was treated with 7.9 g (54.4 mmol) of 4-formyl-indole and stirring was continued at 40° C. for 16 h. The mixture was treated again with 10.0 g (23.3 mmol) of the Wittig salt and 8.0 ml (24.0 mmol) of tetramethyl guanidine and stirring was continued at 40° C. for 24 h after which time the conversion was complete. The reaction mixture was poured into crashed ice and then extracted twice with MeCl2. The organic layer was washed with water, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica (n-heptane/AcOEt, 95:5 to 4:1) to give 15.12 g of the title compound as a light yellow solid.

後処理

  1. stirringstirring
  2. waitwas continued at 40° C. for 24 h
  3. additionThe reaction mixture was poured
  4. extractionextracted twice with MeCl2
  5. washThe organic layer was washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was chromatographed on silica (n-heptane/AcOEt, 95:5 to 4:1)

出典と根拠

ORDレコード
ord-5c81a3b3502a410b88b65a8da4ebe4d9
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07098228B2

反応ノート

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