반응 #470416

ord-0a73d515d71e4b24b09f8bc0019c1b5e

반응 방정식

O
water
NCc1ccccc1
Benzylamine
Oc1cccc(C2=Cc3ccc(O)cc3OC2)c1
3′,7-Dihydroxyisoflav-3-ene
CCO
ethanol
C=O
formaldehyde
Oc1cccc(C2=Cc3cc4c(cc3OC2)OCN(Cc2ccccc2)C4)c1
title compound
Oc1cccc(C2=Cc3cc4c(cc3OC2)OCN(Cc2ccccc2)C4)c1
3-(3-Benzyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타Reaction mixture
  2. 2
    추출then extracted with ethyl acetate (3×30 ml)
  3. 3
    기타chromatographed

실험 절차

3′,7-Dihydroxyisoflav-3-ene (100 mg, 0.42 mmol) was dissolved in ethanol (4 ml). Benzylamine (0.14 ml, 1.28 mmol) was added followed by formaldehyde solution (0.42 ml, 5.59 mmol, 37% wt.). The reaction was stirred at room temperature for 1 day. Reaction mixture was poured into water (50 ml) then extracted with ethyl acetate (3×30 ml) and the combined organic layers reduced. The solid was flash chromatographed using 100% dichloromethane. Fractions 6-12 were combined and reduced to afford the title compound.

출처

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