Reaction #470425

ord-c7ba77a0a2584e1e85322b012ec9bb23

Reaction equation

Oc1ccc(C2=Cc3ccc(O)cc3OC2)cc1
4′,7-Dihydroxyisoflav-3-ene
CCO
ethanol
CC(C)(C)c1ccc(N)cc1
4-tert-Butylaniline
C=O
formaldehyde
→
CC(C)(C)c1ccc(N2COc3cc4c(cc3C2)C=C(c2ccc(O)cc2)CO4)cc1
title compound
Yield 15.0%
CC(C)(C)c1ccc(N2COc3cc4c(cc3C2)C=C(c2ccc(O)cc2)CO4)cc1
4-(3-(4-tert-Butylphenyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol
Yield 15.0%

Reactants

Oc1ccc(C2=Cc3ccc(O)cc3OC2)cc1
4′,7-Dihydroxyisoflav-3-ene
CCO
ethanol
CC(C)(C)c1ccc(N)cc1
4-tert-Butylaniline
C=O
formaldehyde

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe white precipitate was collected

Procedure

4′,7-Dihydroxyisoflav-3-ene (500 mg, 2.08 mmol) was dissolved in absolute ethanol (10 mL). 4-tert-Butylaniline (311 mg, 2.08 mmol) was added followed by formaldehyde solution (6 mL, 0.04 mol, 37 wt. %). The reaction was stirred at room temperature for 1 day. The white precipitate was collected to afford the title compound (134 mg, 15%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08367659B2uspto-grants-2013_02