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1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 2-(4-acetoxyphenyl)-3-(5-cyano-2-benzofuranyl)acrylate

HRID 1901329
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HRID 1901329 반응식
[Cl-].[C:2]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([CH2:12][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:9][C:8]=2[CH:32]=1)#[N:3].[C:33]([O:36][C:37]1[CH:42]=[CH:41][C:40]([C:43](=O)[C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:39][CH:38]=1)(=[O:35])[CH3:34].C1CCN2C(=NCCC2)CC1>O1CCCC1.C(O)C>[C:33]([O:36][C:37]1[CH:42]=[CH:41][C:40]([C:43](=[CH:12][C:10]2[O:11][C:7]3[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:32][C:8]=3[CH:9]=2)[C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:39][CH:38]=1)(=[O:35])[CH3:34]
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참가 물질

6

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10977426Ethyl 4-acetoxybenzoylformateHCID 21844326(5-Cyano-2-benzofuranyl)methyltriphenylphosphonium chloride

생성물 1

HCID 53786787Ethyl 2-(4-acetoxyphenyl)-3-(5-cyano-2-benzofuranyl)acrylate수율 85.6%

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

15.93 g of (5-cyano-2-benzofuranyl)methyltriphenylphosphonium chloride and 8.29 g of ethyl 2-(4-acetoxyphenyl)-2-oxoacetate were dissolved in a mixture solution of 80 ml of tetrahydrofuran and 80 ml of ethanol. At room temperature, 5.34 g of 1,8-diazabicyclo[5.4.0]-7-undecene was added to the above solution, and the mixture was stirred for 18 hours at the same temperature. The resulting reaction solution was concentrated to dryness, and the residue was purified by silica gel column chromatography using a toluene/ethyl acetate mixture as an eluant to obtain 11.28 g of ethyl 2-(4-acetoxyphenyl)-3-(5-cyano-2-benzofuranyl)acrylate in the form of light yellow crystals as a mixture of E and Z forms.

후처리

  1. customThe resulting reaction solution
  2. concentrationwas concentrated to dryness
  3. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ca988291079244ce938962bc5461653f
출처 데이터셋
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05576343

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