Réaction #470410

Équation de réaction

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

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was refluxed for approximately 7 hours
2. 2
   Températureafter cooling to room temperature the volume
3. 3
   Concentrationwas concentrated in vacuo
4. 4
   workup.WAITThe mixture was left in the fridge
5. 5
   Autreto crystallise
6. 6
   AutreThe yellow solid was collected under suction
7. 7
   Autrethe filtrate evaporated to dryness

Mode opératoire

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%).

Source