1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-(4-Benzyloxy-benzofuran-7-yl)-2Z-ethoxy-acrylic acid ethyl ester

HRID 479195ノート

反応式

HRID 479195 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].C1CCN2C(=NCCC2)CC1.[CH2:41]([O:48][C:49]1[C:54]2[CH:55]=[CH:56][O:57][C:53]=2[C:52]([CH:58]=O)=[CH:51][CH:50]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C1COCC1>[CH2:9]([O:8][C:6](=[O:7])/[C:5](/[O:4][CH2:2][CH3:3])=[CH:58]/[C:52]1[C:53]2[O:57][CH:56]=[CH:55][C:54]=2[C:49]([O:48][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[CH:50][CH:51]=1)[CH3:10]

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)2 回HCID 226476054-Benzyloxy-benzofuran-7-carbaldehyde

生成物 1

HCID 686170643-(4-Benzyloxy-benzofuran-7-yl)-2Z-ethoxy-acrylic acid ethyl ester収率 69%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension of (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride (2.04 g, 4.8 mmol) and DBU (0.8 g, 5.2 mmol) in THF (40 ml) was stirred for 10 min at ambient temperature under an argon atmosphere [for the preparation of (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride see: K. K. Bach, H. R. El-Seedi, H. M. Jensen, H. B. Nielsen, I. Thomson, K. B. G. Torssell, Tetrahedron 1994, 50, 7543-7556]. 4-Benzyloxy-benzofuran-7-carbaldehyde (0.8 g, 3.2 mmol) was added and the mixture was heated under reflux for 12 h. The solvent was concentrated at reduced pressure, the residue taken up with ethyl acetate, washed with saturated aqueous NH4Cl solution and two times with brine. The organic layer was dried over sodium sulfate, the solvent removed under reduced pressure and the residue purified by column chromatography (silica gel, hexane/AcOEt=9/1) to give 0.8 g (2.2 mmol, 69%) of the title compound as colorless oil.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 h
  3. concentrationThe solvent was concentrated at reduced pressure
  4. washwashed with saturated aqueous NH4Cl solution and two times with brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe solvent removed under reduced pressure
  7. customthe residue purified by column chromatography (silica gel, hexane/AcOEt=9/1)

出典と根拠

ORDレコード
ord-c134086984bb4904b030b4881901d2ac
出典データセット
uspto-grants-2003_11
特許番号
US06642389B2

反応ノート

読み込み中…