Methyl iodide → Methyl 4-ethenylbenzoate

HRID 265433

반응식

HRID 265433 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 583124Methyl 4-ethenylbenzoate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-6e4a26bd8d5a4022b8d2fcb68fe5ff96
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648385

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