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Triethylamine → (E)-3-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-acrylic Acid Methyl Ester

HRID 220889
ノート
印刷プレビュー

反応式

HRID 220889 の反応式
[CH3:1][O:2][C:3](/[CH:5]=[CH:6]/[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)=[O:4].[NH:16]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]2[CH:23]=[CH:24][CH:25]=[CH:26][C:17]1=2.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][O:2][C:3](=[O:4])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[CH:9][C:10]([C:11]([N:16]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]3[CH:23]=[CH:24][CH:25]=[CH:26][C:17]2=3)=[O:13])=[CH:14][CH:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 5765032,3,4,5-tetrahydro-1H-1-benzazepineHCID 106083304-((1E)-3-methoxy-3-oxoprop-1-en-1-yl)benzoic acid

生成物 1

HCID 57555201(E)-3-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-acrylic Acid Methyl Ester収率 48%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6344
Dichloromethane
溶媒

実験手順

WSCD (1.17 g, 6.16 mmol) was added to a solution of 4-((E)-2-methoxycarbonyl-vinyl)-benzoic acid from Example E65.1 (740 mg, 3.59 mmol), 2,3,4,5-tetrahydro-1H-benzo[b]azepine (445 mg, 3.02 mmol) and DMAP (370 mg, 3.02 mmol) in dichloromethane (40 ml) and triethylamine (0.7 ml, 5.02 mmol). The mixture was heated at reflux for 42 h then solvents were concentrated in vacuo. The residue was dissolved in EtOAc, washed with 1M KHSO4 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 30% EtOAc:70% pet. ether) to yield the title compound (484 mg, 48%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 42 h
  3. concentrationsolvents were concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with 1M KHSO4
  6. dry with materialbrine, dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (eluant; 30% EtOAc:70% pet. ether)

出典と根拠

ORDレコード
ord-008e0e4bc9b541838f2fecdfa52d7a8d
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202858B2

反応ノート

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