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Nitrogen → 4-Hydroxy-3-phenoxy-6-phenyl-2H-pyran-2-one

HRID 613117
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인쇄 미리보기

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HRID 613117 반응식
C([O:3][C:4](=O)[CH:5]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6](OCC)=[O:7])C.[C:19]1([C:25]([O:27][Si](C)(C)C)=[CH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.N#N>CCCCCC.C(OCC)(=O)C>[OH:7][C:6]1[CH:26]=[C:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:27][C:4](=[O:3])[C:5]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 947NitrogenHCID 117406Benzene, [1-[(trimethylsilyl)oxy]ethenyl]-HCID 23051671,3-Diethyl 2-phenoxypropanedioate

생성물 1

HCID 546813824-Hydroxy-3-phenoxy-6-phenyl-2H-pyran-2-one수율 18.3%

시약·촉매·용매 1

HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
100 °C

실험 절차

To a is pressure reactor was added 2-phenoxypropanedioicacid diethylester 8.11 g (0.032 moles) and 1-phenyl-1-(trimethylsilyloxy)ethylene 12.35 g (0.064 moles). The vessel was pressurized to 600 psi with N2. The mixture was heated at 100° C. for 8 hours then an additional 63.5 hours at 147-154° C. The vessel was cooled to room temperature and rinsed with ethyl acetate. Crude flash chromatography (hexane/ethyl acetate 1/1) afforded partially purified material which was then flashed on silica gel using hexane/ethyl acetate 95/5-40/60 as eluents. The resulting solid was recrystallized from diethyl ether and ethyl acetate to afford 1.64g (18%) of the title compound (mp=215-219° C.). 1H NMR (400 MHz, DMSO-d6) δ6.90 (s, 1 H), 6.95 (dd, 2 H), 7.02 (t, 1 H), 7.28-7.33 (m, 2 H), 7.52-7.56 (m, 3 H), 7.80-7.856 (m, 2 H), 12.0 (bs, 1 H).

후처리

  1. customan additional 63.5 hours
  2. customat 147-154° C
  3. temperatureThe vessel was cooled to room temperature
  4. washrinsed with ethyl acetate
  5. customCrude flash chromatography (hexane/ethyl acetate 1/1) afforded partially purified material which
  6. customThe resulting solid was recrystallized from diethyl ether and ethyl acetate

출처 및 근거

ORD 기록
ord-01333eafc46d44069e6c0fe443f993c4
출처 데이터셋
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06005103

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