1,1,3,3-Tetramethylguanidine → (Z)-2-Ethoxy-3-(1H-indol-5-yl)-acrylic Acid Ethyl Ester

HRID 2181182ノート

反応式

HRID 2181182 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:41]=[C:42]2[C:46](=[CH:47][CH:48]=1)[NH:45][CH:44]=[CH:43]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:41]=[C:42]2[C:46](=[CH:47][CH:48]=1)[NH:45][CH:44]=[CH:43]2)[CH3:10]

参加物

5

反応物 3

HCID 664601,1,3,3-Tetramethylguanidine2 回HCID 589040Indole-5-carboxaldehydeHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)

生成物 1

HCID 53309301(Z)-2-Ethoxy-3-(1H-indol-5-yl)-acrylic Acid Ethyl Ester収率 94.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 25.73 g of (1,2-diethoxy-2-oxoethyl)triphenyl phosphonium chloride in 200 ml of dichloromethane was added at 0° C. 8.0 ml of tetramethyl guanidine and the mixture was warmed to 22° C. The mixture was treated with 5.81 g of 5-formyl-indole and stirring was continued at 40° C. for 16 h. The mixture was treated again with 25.73 g of the Wittig salt and 8.0 ml of tetramethyl guanidine and stirring was continued at 40° C. for 24 h after which time the conversion was complete. The mixture was evaporated and the residue partitioned between AcOEt and water. The organic layer was dried, evaporated and the residue chromatographed on silica (n-hexane/AcOEt, 2:1) to give 9.80 g of the title compound as an oil which solidified on storing at 22° C. to give a pale yellow solid. MS: (M)+ 259.2.

後処理

  1. stirringstirring
  2. waitwas continued at 40° C. for 24 h
  3. customThe mixture was evaporated
  4. customthe residue partitioned between AcOEt and water
  5. customThe organic layer was dried
  6. customevaporated
  7. customthe residue chromatographed on silica (n-hexane/AcOEt, 2:1)

出典と根拠

ORDレコード
ord-fa557c8a5d664180ae77c10be72b8998
出典データセット
uspto-grants-2005_05
特許番号
US06890947B2

反応ノート

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