Reacción #470410

Ecuación de reacción

ethanol

4′,7-Dihydroxyisoflav-3-ene

benzylamine

formaldehyde

dehydroequol

ethanol

→

title compound

4-(3-Benzyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was refluxed for approximately 7 hours
2. 2
   Temperaturaafter cooling to room temperature the volume
3. 3
   Concentraciónwas concentrated in vacuo
4. 4
   workup.WAITThe mixture was left in the fridge
5. 5
   Otroto crystallise
6. 6
   OtroThe yellow solid was collected under suction
7. 7
   Otrothe filtrate evaporated to dryness

Procedimiento

4′,7-Dihydroxyisoflav-3-ene (0.47 g, 1.97 mmol) was dissolved in ethanol (ca. 40 mL) and heated to 80-90° C. A solution of benzylamine (0.44 mL, 3.5 mmol) and 37% formaldehyde (0.35 mL, 12.7 mmol) in ethanol (ca. 20 mL) was added to the dehydroequol solution. The reaction mixture was refluxed for approximately 7 hours and after cooling to room temperature the volume was concentrated in vacuo. The mixture was left in the fridge to crystallise. The yellow solid was collected under suction and the filtrate evaporated to dryness to obtain a second crop of the title compound, (combined yield 0.17 g, 23%).

Fuente