تفاعل #62087

معادلة التفاعل

diethyl ether

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

tetrafluoroboric acid

Butyl nitrite

→

title compound

المردود 100.7%

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

المردود 100.7%

المذيبات

ethanol

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةbefore being cooled to 0° C
2. 2
   أخرىto form
3. 3
   ترشيحThe solid was collected by filtration
4. 4
   غسيلwashed with cold diethylether (30 ml)
5. 5
   workup.STIRRINGThe reaction was stirred for 12 hours
6. 6
   ترشيحfiltered
7. 7
   غسيلThe filtrant was washed with water
8. 8
   أخرىdried in a desiccator
9. 9
   أخرىused without further purification

الإجراء التجريبي

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

المصدر