1-Methoxybuta-1,3-diene → 4-{2-[(e)-2-Methoxyethenyl]-2,3-dihydro-1-benzofuran-5-yl}benzonitrile

HRID 1064710

反応式

HRID 1064710 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1I.[CH3:17][O:18][CH:19]=[CH:20][CH:21]=[CH2:22].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(Cl)Cl.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:17][O:18]/[CH:19]=[CH:20]/[CH:21]1[CH2:22][C:3]2[CH:4]=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=3)[CH:6]=[CH:7][C:2]=2[O:1]1

参加物

8

反応物 3

HCID 182131-Methoxybuta-1,3-dieneHCID 516892Sodium BicarbonateHCID 103586764-(4-Hydroxy-3-iodophenyl)benzonitrile

生成物 1

HCID 222746034-{2-[(e)-2-Methoxyethenyl]-2,3-dihydro-1-benzofuran-5-yl}benzonitrile収率 549.9%

試薬・触媒・溶媒 4

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
23 °C

実験手順

A solution of Example 1A (0.20 g, 0.623 mmol), 1-methoxybutadiene (0.18 g, 2.18 mmol), palladium diacetate (0.007 g, 0.031 mmol), sodium bicarbonate (0.261 g, 3.11 mmol) and tetrabutyl ammonium chloride (0.173 g, 0.623 mmol) was heated at 60° C. in DMF (3 mL) under an atmosphere of nitrogen for 36 hours. The reaction was cooled to 23° C., diluted with CH2Cl2 (50 mL), filtered through Celite. The solution was concentrated under reduce pressure and the residue was purified on silica using CH2Cl2 to give the titled compound (0.95 g, 55%). 1H NMR (CDCl3): 3.05 (m, 1H), 3.40 (m, 1H), 3.60 (s, 3H), 5.00 (m, 1H), 5.22 (m, 1H), 6.72 (d, J=14 Hz, 1H), 6.83 (d, J=7 Hz, 1H), 7.38 (m, 2H), 7.65 (m, 4H); MS (DCI): 278 (M+H+), 295 (M+NH4+).

後処理

  1. filtrationfiltered through Celite
  2. concentrationThe solution was concentrated
  3. customthe residue was purified on silica

出典と根拠

ORDレコード
ord-dc0a3a54a55d49d59e592bf06816222b
出典データセット
uspto-grants-2005_11
特許番号
US06969730B2

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