Реакция #62087

Уравнение реакции

diethyl ether

2-(7-Amino-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one

tetrafluoroboric acid

Butyl nitrite

→

title compound

Выход 100.7%

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

Выход 100.7%

Растворители

ethanol

water

Условия реакции

Обработка

1. 1
   Температураbefore being cooled to 0° C
2. 2
   Другоеto form
3. 3
   ФильтрацияThe solid was collected by filtration
4. 4
   Промывкаwashed with cold diethylether (30 ml)
5. 5
   workup.STIRRINGThe reaction was stirred for 12 hours
6. 6
   Фильтрацияfiltered
7. 7
   ПромывкаThe filtrant was washed with water
8. 8
   Другоеdried in a desiccator
9. 9
   Другоеused without further purification

Методика

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

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