Cyclopentadiene → (2-Oxa-3-azabicyclo[2.2.1]hept-5-en-3-yl)-phenylmethanone

HRID 351363

반응식

HRID 351363 반응식
I([O-])(=O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[CH:23]1[CH2:27][CH:26]=[CH:25][CH:24]=1.[C:28]([NH:36][OH:37])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(OCC)(=O)C>ClCCl>[CH:24]12[CH2:23][CH:27]([CH:26]=[CH:25]1)[N:36]([C:28]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:35])[O:37]2

참가 물질

6

반응물 4

HCID 7612CyclopentadieneHCID 8857Ethyl AcetateHCID 10313Benzohydroxamic acidHCID 2724292Tetrabutylammonium Periodate

생성물 1

HCID 328016(2-Oxa-3-azabicyclo[2.2.1]hept-5-en-3-yl)-phenylmethanone수율 78%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Tetra-n-butylammonium periodate (17.3 g, 39.9 mmol) was added to a solution of freshly cracked cyclopentadiene (4.00 g, 60.6 mmol) in dichloromethane (150 cm3). Benzohydroxamic acid (5.50 g, 40.1 mmol) was then added portionwise over 5 minutes and the solution was stirred overnight at room temperature. Upon completion of reaction, the organic solution was washed successively with sodium thiosulfate (10% aq. soln., 2×400 cm3) and sodium hydrogen carbonate (sat'd. aq., 500 cm3), then dried over anhydrous magnesium sulfate, filtered and concentrated to give a crude black oil. Flash chromatography (SiO2, 40% ethyl acetate in petrol) gave the bicyclic adduct 7 (6.23 g, 31.0 mmol, 78%) as a light brown oil, which solidified upon standing at room temperature; δH (250 MHz, CDCl3) 7.75 (2H, m, ArH), 7.52–7.37 (3H, m, ArH), 6.50 (1H, m, CH═CH), 6.37 (1H, m, CH═CH), 5.35 (1H, m, CHNBz), 5.28 (1H, m, CHON), 2.13 (1H, dt, J 8.6 & 1.9 Hz, CHH), 1.84 (1H, m, CHH).

후처리

  1. customUpon completion of reaction
  2. washthe organic solution was washed successively with sodium thiosulfate (10% aq. soln., 2×400 cm3) and sodium hydrogen carbonate (sat'd. aq., 500 cm3)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude black oil

출처 및 근거

ORD 기록
ord-e327822538fd4becbc1a2b05b22b1a4c
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183440B2

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