Methyl iodide → Methyl 4-ethenylbenzoate

HRID 265433

反応式

HRID 265433 の反応式
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[CH2:2].N12CCCN=C1CCCC[CH2:13]2.IC.C(OCC)(=O)C>C(#N)C>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:13])=[O:8])=[CH:5][CH:4]=1)=[CH2:2]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 140984-Vinylbenzoic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

生成物 1

HCID 583124Methyl 4-ethenylbenzoate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 4-vinylbenzoic acid (Aldrich, 2.18 g, 14.7 mmol) in anhydrous acetonitrile (14.0 mL) was added 1.8-diazabicyclo [5.4.0]undec-7-ene (Aldrich, 2.46 g, 16.2 mmol) and iodomethane (Aldrich, 3.13 g, 22.1 mmol) at 0° C. The reaction mixture was then warmed to room temperatue and allowed to stir for 3 h. Ethyl acetate (100 mL) was added to the mixture and the solution was washed with brine (50 mL). The organic phase was then separated and concentrated in vacuo. The residue was chromatographed on silica gel (eluted with 5% ethyl acetate in hexane) to give 1.05 g (Y: 44%) of the title product; 1H-NMR (CDCl3): δ 8.00 (d,J=8.4 Hz, 2H), 7.47 (d, J=8.4 Hz, 2H), 6.76 (m, 1H), 5.87 (d, J=17.6 Hz, 1H), 5.38 (d, J=11.0 Hz, 1H), 3.91 (s, 3H); MS (DCI) m/e: 163 (MH+).

後処理

  1. temperatureThe reaction mixture was then warmed to room temperatue
  2. washthe solution was washed with brine (50 mL)
  3. customThe organic phase was then separated
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (eluted with 5% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-6e4a26bd8d5a4022b8d2fcb68fe5ff96
出典データセット
uspto-grants-1997_07
特許番号
US05648385

関連ノート

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