Reaktion #10207

Reaktionsgleichung

1-(5,14-diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,7,9-tetraen-6-one-10-yl)-2,2,2-trifluoro-ethanone

POCl3

→

1-(6-Chloro-5,14-diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaen-10-yl)-2,2,2-trifluoro-ethanone

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter concentration in vacuo
2. 2
   workup.ADDITIONthe residue was diluted with CH2Cl2 (15 mL)
3. 3
   workup.ADDITIONcarefully treated with saturated NaHCO3 solution (10 mL)
4. 4
   workup.STIRRINGwith stirring
5. 5
   Sonstigewas separated
6. 6
   Extraktionthe aqueous layer extracted CH2Cl2 (3 times)
7. 7
   WaschenThe organic layer was washed with H2O and saturated NaCl solution
8. 8
   Filtrationfiltered through cotton
9. 9
   Einengenconcentrated to a brown oil (217 mg, 93%)

Vorschrift

1-(5,14-diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,7,9-tetraen-6-one-10-yl)-2,2,2-trifluoro-ethanone (156 mg, 0.49 mmol) was treated with POCl3 (5 mL) and warmed to 100° C. with stirring for 3 hours. After concentration in vacuo, the residue was diluted with CH2Cl2 (15 mL) and carefully treated with saturated NaHCO3 solution (10 mL) with stirring. Once CO2 evolution slowed the mixture was separated and the aqueous layer extracted CH2Cl2 (3 times). The organic layer was washed with H2O and saturated NaCl solution, filtered through cotton and concentrated to a brown oil (217 mg, 93%). (TLC ethyl acetate, Rf 0.3) 1H NMR (400 MHz, 2HCCl3) δ 8.03 (d, J=8.5 Hz, 1H), 7.83 (s, 1H), 7.62 (s, 1H), 7.35 (d, J=8.5 Hz, 1H), 4.43 (m, 1H), 4.01 (m, 1H), 3.62 (m, 1H), 3.29 (m, 2H), 3.23 (m, 1H), 2.45 (m, 1H), 2.10 (d, J=11.6 Hz, 1H). APCI MS m/e 341.1 [(M+1)+].

Quelle