반응 #470411

ord-b6c6448adf474d74b28f8268ff7e64f2

반응 방정식

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

반응 조건

온도
85°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도The reaction mixture was refluxed for approximately 7 hours
  2. 2
    온도after cooling to room temperature the volume
  3. 3
    농축was concentrated in vacuo
  4. 4
    workup.WAITThe mixture was left in the fridge
  5. 5
    기타to crystallise
  6. 6
    기타The yellow solid was collected under suction
  7. 7
    기타the filtrate evaporated to dryness

실험 절차

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%).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08367659B2uspto-grants-2013_02