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

HRID 361898ノート

反応式

HRID 361898 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-40006dedb6b54c95b84cea1d60297a1a
出典データセット
uspto-grants-1999_02
特許番号
US05866577

反応ノート

読み込み中…