Diethyl Ether → 2-(7-Hydroxy-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one

HRID 33809

Reaktionsgleichung

Reaktionsgleichung von HRID 33809
N[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[S:12][C:11]1[C:10]([C:16]3[O:17][C:18]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:19][C:20](=[O:22])[CH:21]=3)=[CH:9][CH:8]=[CH:7][C:6]=1[S:5]2.F[B-](F)(F)F.[H+].N(OCCCC)=[O:36].C(OCC)C>C(O)C.O>[OH:36][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[S:12][C:11]1[C:10]([C:16]3[O:17][C:18]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[CH:19][C:20](=[O:22])[CH:21]=3)=[CH:9][CH:8]=[CH:7][C:6]=1[S:5]2

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 10996Butyl nitriteHCID 28118Tetrafluoroboric acidHCID 597974272-(7-Amino-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one

Produkt 1

HCID 597974292-(7-Hydroxy-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-oneAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-(7-Amino-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one (21) (575 mg, 1.4 mmol) was suspended in ethanol (5 mL) was added tetrafluoroboric acid (54 wt % in ether, 3 ml, 1.68 mmol). The mixture was stirred at room temperature for 10 minutes before being cooled to 0° C. Butyl nitrite (220 μl, 2.8 mmol) was then added dropwise and the mixture stirred for 30 minutes before the addition of diethyl ether (40 ml) which caused a precipitate to form. The solid was collected by filtration and washed with cold diethylether (30 ml) then added to a solution of cupric nitrate trihidrate (210 g, 870 mmol) and cuprous oxide (190 mg, 1.31 mmol) in water (300 ml). The reaction was stirred for 12 hours and then filtered. The filtrant was washed with water, dried in a desiccator and used without further purification give the title compound (0.58 g, 100%). NMR (300 MHz, CDCl3): δH=10.08 (1H, bs); 7.76 (1H, dd); 7.60 (1H, dd); 7.46 (1H, dd); 7.35 (1H, dd); 7.02 (1H, d); 6.74 (1H, dd); 6.24 (1H, d); 5.55 (1H, d); 3.69 (H, m), 3.36 (4H, m); m/z (LC-MS, ESP), RT=3.83 min, (M++1)=412

Aufarbeitung

  1. temperaturebefore being cooled to 0° C
  2. customto form
  3. filtrationThe solid was collected by filtration
  4. washwashed with cold diethylether (30 ml)
  5. stirringThe reaction was stirred for 12 hours
  6. filtrationfiltered
  7. washThe filtrant was washed with water
  8. customdried in a desiccator
  9. customused without further purification

Quellen und Nachweise

ORD-Eintrag
ord-b92d9026764d4d1fb0183695bfbe077d
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429660B2

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