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

HRID 613117

反応式

HRID 613117 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-01333eafc46d44069e6c0fe443f993c4
出典データセット
uspto-grants-1999_12
特許番号
US06005103

関連ノート

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