反应 #470410

ord-c6eb609a9c764f31bf1e3a52ab7d10d8

反应方程式

CCO
ethanol
Oc1ccc(C2=Cc3ccc(O)cc3OC2)cc1
4′,7-Dihydroxyisoflav-3-ene
NCc1ccccc1
benzylamine
C=O
formaldehyde
Oc1ccc(C2=Cc3ccc(O)cc3OC2)cc1
dehydroequol
CCO
ethanol
Oc1ccc(C2=Cc3cc4c(cc3OC2)OCN(Cc2ccccc2)C4)cc1
title compound
Oc1ccc(C2=Cc3cc4c(cc3OC2)OCN(Cc2ccccc2)C4)cc1
4-(3-Benzyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol

反应条件

温度
85°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度The reaction mixture was refluxed for approximately 7 hours
  2. 2
    温度after cooling to room temperature the volume
  3. 3
    浓缩was concentrated in vacuo
  4. 4
    workup.WAITThe mixture was left in the fridge
  5. 5
    其他to crystallise
  6. 6
    其他The yellow solid was collected under suction
  7. 7
    其他the filtrate evaporated to dryness

实验过程

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%).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08367659B2uspto-grants-2013_02