反应 #470411

ord-b6c6448adf474d74b28f8268ff7e64f2

反应方程式

Oc1ccc(C2=Cc3ccc(O)cc3OC2)cc1
4′,7-Dihydroxyisoflav-3-ene
CCO
ethanol
CNCc1ccccc1
methylbenzylamine
C=O
formaldehyde
Oc1ccc(C2=Cc3ccc(O)cc3OC2)cc1
dehydroequol
CCO
ethanol
CC(c1ccccc1)N1COc2cc3c(cc2C1)C=C(c1ccc(O)cc1)CO3
title compound
CC(c1ccccc1)N1COc2cc3c(cc2C1)C=C(c1ccc(O)cc1)CO3
4-(3-(1-Phenylethyl)-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 (0.45 g, 1.87 mmol) was dissolved in ethanol (ca 40 mL) and heated to 80-90° C. A solution of methylbenzylamine (0.44 mL, 4.03 mmol) and 37% formaldehyde (0.35 mL, 123 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