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

HRID 2181184
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HRID 2181184 반응식
[Cl-].[CH3:2][O:3][CH:4]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C)C(=N)N(C)C.[CH:42]([C:44]1[CH:45]=[C:46]2[C:50](=[CH:51][CH:52]=1)[NH:49][CH:48]=[CH:47]2)=O>ClCCl>[CH2:7]([O:6][C:5](=[O:14])/[C:4](/[O:3][CH3:2])=[CH:42]/[C:44]1[CH:45]=[C:46]2[C:50](=[CH:51][CH:52]=1)[NH:49][CH:48]=[CH:47]2)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 664601,1,3,3-Tetramethylguanidine2회HCID 589040Indole-5-carboxaldehydeHCID 18003490(Benzyloxycarbonyl-methoxy-methyl)-triphenyl-phosphonium chloride

생성물 1

HCID 69563356(Z)-3-(1H-indol-5-yl)-2-methoxy-acrylic Acid Benzyl Ester수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3.70 g of (1-methoxy-2-benzyloxy-oxoethyl)triphenyl phosphonium chloride in 60 ml of dichloromethane was added at 0° C. 1.07 ml of tetramethyl guanidine and the mixture was warmed to 22° C. The mixture was treated with 2.25 g of 5-formyl-indole and stirring was continued at 40° C. for 16 h. The mixture was treated again with 3.70 g of the Wittig salt and 1.07 ml of tetramethyl guanidine and stirring was continued at 40° 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, 4:1) to give 1.67 g of the title compound as a pale yellow oil. MS: (M+H)+ 308.2.

후처리

  1. stirringstirring
  2. waitwas continued at 40° 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, 4:1)

출처 및 근거

ORD 기록
ord-071c3d8eeaf0428693bce329c87eaaf9
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06890947B2

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